4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane | Epoxides

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Quality Control of 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane Purity: 99% SDS Specification

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NMR

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Product Details of 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

CAS No. :	57280-22-5
Formula :	C₇H₁₂O₃
M.W :	144.17
SMILES Code :	CC1(C)OCC2OC2CO1
MDL No. :	MFCD16621162
Boiling Point :	No data available
InChI Key :	GEKNCWQQNMEIMS-UHFFFAOYSA-N
Pubchem ID :	11094747

Safety of 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P501-P261-P272-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P333+P313

Application In Synthesis of 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 57280-22-5 ]

[ 57280-22-5 ] Synthesis Path-Downstream 1~35

1
[ 57280-22-5 ]
[ 72791-83-4 ]
[ 72791-80-1 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1979,vol. 33,p. 587 - 589.

2
[ 57280-22-5 ]
[ 72791-83-4 ]
[ 72791-81-2 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1979,vol. 33,p. 587 - 589.

3
[ 57280-22-5 ]
[ 72791-83-4 ]
[ 72791-82-3 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1979,vol. 33,p. 587 - 589.

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[ 1003-83-4 ]
[ 57280-22-5 ]

Yield	Reaction Conditions	Operation in experiment
85.2%	With disodium hydrogenphosphate; dihydrogen peroxide; sodium hydroxide; In methanol; water; acetonitrile; at 60 - 80℃;pH 7 - 9.5;Large scale; Green chemistry;	1) To the reaction vessel was charged 1810 kg of compound A-3, 1730 kg of acetonitrile, 1480 kg of methanol and 1920 kgOf water, then add 15. lkg of disodium hydrogen phosphate; stirring heating reaction solution;(3) The reactor was charged with 1990 kg of 27% hydrogen peroxide, and 1M aqueous sodium hydroxide solution 1086 kg, temperature control60-80 C; the reaction process to control the pH value of 7-9.5; reaction reactor in the reactor for 8 to 9 hours after stirring to room temperature;(5) In the reaction kettle, 2880kg of saturated brine and 6335kg of methylene chloride were added in this order, and the organic phase was stirred and separated into organic phase. 4010kg of sodium sulfite solution was added. The organic phase was stirred and dried, (2) After drying, the organic phase was filtered and the solvent was distilled off at 40 C to obtain crude compound of compound A.(3) The crude compound A was distilled under reduced pressure to give the product A (1820 kg, total yield: 85.2%). The purity of the obtained Compound A showed that the purity of the compound A was 99.6% or more.
85%	With disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 18h;Inert atmosphere;	To a solution of 6 (10.0 g, 78 mmol) in DCM (400 mL) m-CPBA (27.0 g, 156 mmol) and finely powdered Na2HPO4 (12.7 g, 90 mmol) were added under argon. The reaction mixture was stirred at room temperature for 18 h, and was then chilled to 0 C. The precipitate was removed by filtration through Celite, and the filtrate was washed sequentially with sat. NaHCO3 (150 mL), sat. Na2S2O3 (150 mL), and then brine. The organic phase was then dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography(EtOAc/hexane 5% to 30%) to afford 7 as a pale yellow oil (9.6 g, 85%). Rf = 0.21 (EtOAc/hexane 20%); 1H NMR (400 MHz, CDCl3): delta 4.06-3.96 (4H, m, H-2 and H-21), 3.21-3.18 (2H, m, H-1), 1.38 (3H, s, H-4 or H-5), 1.32 (3H, s, H-4 or H-5) ppm; 13C NMR (101 MHz, CDCl3): delta102.2 (1C, C-3), 60.0 (2C, C-2), 56.4 (2C, C-1), 24.7 (1C, C-4 or C-5), 23.4 (1C, C-4 or C-5) ppm; Data matches literature
80%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;	A. To a suspension of m-chloroperbenzoic acid (74% pure; 78.15 g; 0.33 mole) in methylene chloride (600 ml), was added a solution of 2,2-dimethyl-4,7-dihydro-1,3-dioxepin (II) (41.0 g, 0.32 mole) in methylene chloride (200 ml) during 30 min at room temperature. The mixture was refluxed for 8 hrs and then cooled in ice for 1 hr. The precipitated solid was filtered off and the organic filtrate was washed with 10% aqueous sodium sulfite (2100 ml), saturated aqueous sodium bicarbonate (3500 ml), 5% aqueous sodium hydroxide (2250 ml) and brine (2200 ml) and dried (MgSO4). Removal of the solvent followed by vacuum distillation of the residual oil gave the epoxide product (III) as a colorless liquid. 36.94 g (80% yield). b.p. 90-92/11 mm. The following is an improved method employing the more economical hydrogen peroxide as the epoxidizing agent.

80%	With sodium hydroxide; tert-butylhypochlorite; sodium hydrogensulfite; In aqueous t-butanol;	D. To an ice-cold (5), stirred solution of the dioxepin (II) (12.81 g, 0.1 mole) in aqueous t-butanol (50%; 50 ml) adjusted to pH 6.0 with dilute sulfuric acid, was added t-butyl hypochlorite (11.3 g, 0.105 mole), while the pH was maintained at 6.0. The reaction mixture was allowed to rise to room temperature and stirred for 4 hrs with protection from light. Sodium bisulfite (200 mg) was added to the reaction mixture, followed by 50% aqueous sodium hydroxide to bring the pH to 12. The reaction mixture was heated at 100 for 1 hr and then cooled. The upper t-butanol layer was separated and the aqueous layer was extracted with t-butanol (3*20 ml). The combined organic layers were dried (Na2 CO3). Solvent removal, followed by fractional distillation, gave the epoxide product (III) as a colorless oil in ?80% yield.
70%	With dihydrogen peroxide; sodium carbonate; In methanol; benzonitrile;	C. To a suspension of sodium carbonate (37 g, 0.35 mole) in a mixture of the dioxepin (II) (158.7 g, 1.26 mole), benzonitrile (127.9 g, 1.26 mole) and methanol (150 ml), was added 30% aqueous hydrogen peroxide (42.2 g, 1.24 mole) during 30 min at such a rate that the temperature stayed below 80. The mixture was kept at 80 with an oil bath for 2 hr, by which time 99% of the hydrogen peroxide added had reacted. The mixture was decanted and, then, subjected to fractional distillation first at 60 mm, then at 20 mm and finally at 6 mm. The fraction boiling at 75-85 at 6 mm was refractionated at 6 mm to obtain the product (III) as a colorless liquid. (125.5 g) (70% yield). b.p. 82-87/6 mm.
67%	With dihydrogen peroxide; sodium carbonate; In methanol; acetonitrile;	B. To a stirred solution of 2,2-dimethyl-4,7-dihydro-1,3-dioxepin (151.4 g, 1.18 mole) in methanol (500 ml) was added anhydrous sodium carbonate (85 g), followed by acetonitrile (150 ml). This suspension was treated with aqueous hydrogen peroxide (30%; 315 ml, 2.78 mole) dropwise at such a rate that the temperature was maintained at 40. After 5 hr. at 40, the reaction mixture was poured into brine (1.5 l) and the solution was extracted with n-butanol. The organic layer was washed with brine, dried, and, then, freed of the solvent in vacuo. Vacuum distillation of the residue yielded the product (III) as a colorless liquid (114 g) (67% yield).
	With disodium hydrogenphosphate; phosphomolybdic acid; dihydrogen peroxide; sodium hydroxide; In methanol; water; at 40 - 60℃; for 3h;pH 8 - 10;	Methanol (90 g, 2.81 mol) was sequentially introduced into the reaction flask.Acetonitrile (100 g, 2.44 mol), pure water (100 g, 5.56 mol),Na2HPO4 (1 g, 0.007 mol) and phosphomolybdic acid (0.3 g),Place in an oil bath and heat and stir.Add 1M NaOH solution to adjust the pH of the system to 8-10.Weighing compound 2 (100 g, 0.78 mol) into the reaction flask,When the reaction solution was heated to 50 C, H 2 O 2 (128 g, 1.13 mol) was slowly added dropwise.The reaction temperature is controlled at 40-60 C; the end of the addition is carried out, and the heat retention reaction is about 3 h.The remaining material is ?1%.Work-up: quench the hydrogen peroxide with 125 g of 20% aqueous sodium sulfite solution.After adding 100 g of saturated brine and 300 g of dichloromethane (DCM), the mixture was shaken well.The liquid phase was separated and the aqueous phase was extracted with DCM (150 g*2). Combine the organic phase,It was then dried over anhydrous sodium sulfate.The organic solvent was concentrated to give a crude product (109 g). Then distilled under reduced pressure, A 4,4-dimethyl-3,5,8-trioxabicyclo[5,1,0]octane product is obtained.

References: [1]Patent: CN106967083,2017,A .Location in patent: Paragraph 0070; 0137-0145.
[2]Beilstein Journal of Organic Chemistry,2017,vol. 13,p. 2883 - 2887.
[3]Synthesis,1980,p. 810 - 811.
[4]Patent: US4341756,1982,A .
[5]Patent: US4341756,1982,A .
[6]Patent: US4341756,1982,A .
[7]Patent: US4341756,1982,A .
[8]Patent: CN108822122,2018,A .Location in patent: Paragraph 0032-0033; 0035-0036; 0038-0039.

5
[ 57280-22-5 ]
[ 993-07-7 ]
[ 201230-82-2 ]
2,2-Dimethyl-5-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-[1,3]dioxepane [ No CAS ]

References: [1]Journal of the American Chemical Society,1984,vol. 106,p. 6093 - 6095.

6
[ 57280-22-5 ]
[ 2408-36-8 ]
[ 141077-78-3 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 1431 - 1434.

7
[ 57280-22-5 ]
[ 141509-49-1 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 3662 - 3672.

8
[ 57280-22-5 ]
[ 108-98-5 ]
(2R^*,3R^*)-1,4-di-O-isopropylidene-3-phenylthio-1,2,4-butanetriol [ No CAS ]

References: [1]Synthesis,1995,p. 1291 - 1294.

9
[ 57280-22-5 ]
(5S,6S)-6-Bromo-2,2-dimethyl-[1,3]dioxepan-5-ol [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 1845 - 1848.
[2]Tetrahedron,1998,vol. 54,p. 2709 - 2722.

10
[ 57280-22-5 ]
(5S,6S)-6-Iodo-2,2-dimethyl-[1,3]dioxepan-5-ol [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 1845 - 1848.
[2]Tetrahedron,1998,vol. 54,p. 2709 - 2722.

11
[ 56-18-8 ]
[ 57280-22-5 ]
6-[3-(3-Amino-propylamino)-propylamino]-2,2-dimethyl-[1,3]dioxepan-5-ol [ No CAS ]