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[ CAS No. 6836-21-1 ]

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Chemical Structure| 6836-21-1
Chemical Structure| 6836-21-1
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CAS No. :6836-21-1 MDL No. :MFCD12756805
Formula : C15H16O3 Boiling Point : 370.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :244.29 g/mol Pubchem ID :13570063
Synonyms :

Safety of [ 6836-21-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6836-21-1 ]

  • Upstream synthesis route of [ 6836-21-1 ]
  • Downstream synthetic route of [ 6836-21-1 ]

[ 6836-21-1 ] Synthesis Path-Upstream   1~9

  • 1
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  • [ 6836-22-2 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With sodium hydroxide; water In methanol at 40℃; for 2 h;
Stage #2: With hydrogenchloride In water
Step 3
(7-Methoxy-naphthalen-1-yl)-acetic acid:
Sodium hydroxide (0.62 g; 15.6 mmol) and water (6 mL) was added to a solution of (7-methoxy-naphthalen-1-yl)-acetic acid ethyl ester (2.38 g; 9.8 mmol) in methanol (12 mL).
Under continuous stirring, the mixture was maintained at about 40° C. for about 2 hours.
The mixture was then concentrated in vacuo, the residue was diluted with water (50 mL), and extracted with ether (4*25 mL).
The aqueous phase was acidified with concentrated hydrochloric acid until a pH of 2 was achieved.
Standard extractive workup afforded the title product as an off-white solid (1.9 g; 90percent yield).
1H NMR (300 MHz, CD3OD) δ 3.9 (s, 3H), 4.03 (s, 2H), 7.15 (dd, J=9.0, 2.4 Hz, 1H), 7.27-7.41 (m, 4H), 7.76 (m, 2H); LC-MS: 215 (M+H)+.
Reference: [1] Patent: US2008/280991, 2008, A1, . Location in patent: Page/Page column 35
[2] Patent: US5612368, 1997, A,
[3] Organic Preparations and Procedures International, 2009, vol. 41, # 2, p. 164 - 168
[4] Patent: EP2474522, 2012, A1, . Location in patent: Page/Page column 7-8
  • 2
  • [ 27533-70-6 ]
  • [ 6836-21-1 ]
YieldReaction ConditionsOperation in experiment
87.3% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 25 - 30℃; for 12 h; To a solution of ethyl-2-(2-methoxynaphthalen-8-yl) acetate(3 g, 12.1 mmol) in anhydrous dichloromethane (45 mL, 15vol) and added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ, 4.15 g, 18.2 mmol) at 15 °C. After addition, the mixturewas stirred at 25-30 °C for 12 h. The mixture was filtered andthe precipitate solid was washed with CH2Cl2 (30 mL, 10 vol),the combined organic phase was washed successively withsaturated NaHCO3 solution (15 mL, 3 × 5 vol), water (15 mL,3 × 5 vol) and followed by brine (15 mL, 3 × 5 vol), organiclayer was dried over Na2SO4. The solvent was removed underreduced pressure to afford brown coloured compound, crudewas purified by column chromatography on 100-200 silicagel using 20 percent ethyl acetate in n-hexane, to obtain colourlessoil (2.59 g, 87.3 percent yield).IR (KBr, νmax, cm–1): 2981, 2937, 2834, 1733, 1627, 1601,1511, 1469, 1450, 1260, 1213, 1159, 133, 832; 1H NMR (400MHz, CDCl3): δ 7.75 (d, J = 8.4 Hz, 1H), 7.71 (d, J = 8.0 Hz,1H) 7.38 (d, J = 7.2 Hz, 1H), 7.30 (t, J = 8.0 Hz, 2H), 7.16(dd, J1 = 2.4 Hz, J2 = 8.8 Hz, 1H), 4.15 (q, J = 7.2 Hz, 2H), 4.0(s, 2H), 3.93 (s, 3H), 1.2 (t, J = 7.2 Hz, 3H); 13C NMR (100Hz,DMSO-d6): δ 171.1, 157.46, 132.99, 130.01, 129.79, 128.74,128.37, 127.25, 123.02, 117.88, 117.88, 102.76, 60.23, 54.94,14.0; EI-MS, m/z (percent): 245 (M + 1, 100), 171 (17).
14 kg With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 15℃; Large scale Add 16Kg of the compound of formula (I) and 170L of dichloromethane, add 50L solution of DDQ16Kg in dichloromethane at 15 °C, drop, incubate for 4~5h, wash with 150L of sodium bicarbonate solution, 150L of brine, anhydrous Dry over sodium sulfateFiltration and concentration of the filtrate to dryness gave the compound of formula (II): 14Kg.
Reference: [1] Organic Preparations and Procedures International, 2009, vol. 41, # 2, p. 164 - 168
[2] Asian Journal of Chemistry, 2016, vol. 28, # 6, p. 1367 - 1370
[3] Patent: CN104276979, 2018, B, . Location in patent: Paragraph 0028; 0030; 0031
  • 3
  • [ 99416-97-4 ]
  • [ 6836-21-1 ]
YieldReaction ConditionsOperation in experiment
95.79% at 215 - 225℃; Example 3: Preparation of 2-(7-methoxynaphthalen-1 -yl) acetic acid ethyl ester (formula V)A mixture of oily mass as obtained in example 2 (40 gm) and sulphur (5.2 gm) was heated at 215-225°C until reaction completes. The reaction mass was cooled at room temperature, ethyl acetate (200 ml) and charcoal (2 gm) were added to reaction mass, and stirred for 30 min at reflux temperature. The reaction mass was cooled and filtered. The organic layer was evaporated to dryness under reduced pressure to obtain product.Weight of oily mass = 38gm (95.79percent yield).
19.2% at 250 - 260℃; for 3 h; Step 2
(7-Methoxy-naphthalen-1-yl)-acetic acid ethyl ester:
In a dehydrogenation system fitted with a ground-glass cold finger condenser and gas inlet and outlet tubes, were placed (1-hydroxy-7-methoxy-1,2,3,4-tetrahydro-naphthalen-1yl)-acetic acid ethyl ester (13.46 g, 51.0 mmol), 10percent palladium on carbon (1.75 g; 13percent by weight), 1,1-diphenylethylene (9.92 g; 55.0 mmol), and 1-methylnaphthalene (37 mL).
Under a continuous flow of nitrogen, the reaction mixture was heated to 250-260° C. (Wood's metal bath) for about 3 hours while steam was passed through the condenser.
The reaction mixture was cooled to ambient temperature, diluted with toluene, filtered, and concentrated in vacuo to give a crude product which was distilled under reduced pressure (oil pump, about 160° C.).
The crude product was purified by flash column chromatography on silica gel (5*16 cm, 5percent ethyl acetate/petroleum ether elution) to give the title product as a yellow oil (2.38 g, 19.2percent).
1H NMR (300 MHz, CDCl3) δ1.21 (t, J=7.2 Hz, 3H), 3.93 (s, 3H), 4.02 (s, 2H), 4.14 (q, J=7.2 Hz, 2H), 7.15 (dd, J=9.0, 2.4 Hz, 1H), 7.29 (m, 3H), 7.38 (d, J=6.9 Hz, 1H), 7.71 (d, J=8.1 Hz, 1H), 7.76 (d, J=9.0 Hz, 1H); GC-MS: 244 (M)+.
Reference: [1] Patent: WO2012/70025, 2012, A1, . Location in patent: Page/Page column 9-10
[2] Journal of Organic Chemistry, 1985, vol. 50, # 26, p. 5550 - 5556
[3] Patent: US2008/280991, 2008, A1, . Location in patent: Page/Page column 34-35
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  • [ 27532-26-9 ]
  • [ 6836-21-1 ]
Reference: [1] Patent: EP2474522, 2012, A1, . Location in patent: Page/Page column 7
  • 5
  • [ 6836-20-0 ]
  • [ 27533-70-6 ]
  • [ 6836-21-1 ]
Reference: [1] Organic Preparations and Procedures International, 2009, vol. 41, # 2, p. 164 - 168
  • 6
  • [ 6836-19-7 ]
  • [ 6836-21-1 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 26, p. 5550 - 5556
[2] Patent: WO2012/70025, 2012, A1,
[3] Patent: EP2474522, 2012, A1,
[4] Patent: CN104276979, 2018, B,
  • 7
  • [ 27533-69-3 ]
  • [ 6836-21-1 ]
Reference: [1] Asian Journal of Chemistry, 2016, vol. 28, # 6, p. 1367 - 1370
  • 8
  • [ 4521-28-2 ]
  • [ 6836-21-1 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 26, p. 5550 - 5556
  • 9
  • [ 7270-63-5 ]
  • [ 64-17-5 ]
  • [ 93-04-9 ]
  • [ 38077-95-1 ]
  • [ 6836-21-1 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 17, p. 7760 - 7770
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