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Chemical Structure| 3587-60-8 Chemical Structure| 3587-60-8
Chemical Structure| 3587-60-8

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Product Details of Benzyl chloromethyl ether

CAS No. :3587-60-8
Formula : C8H9ClO
M.W : 156.60
SMILES Code : ClCOCC1=CC=CC=C1
MDL No. :MFCD00000886
InChI Key :LADPCMZCENPFGV-UHFFFAOYSA-N
Pubchem ID :137983

Safety of Benzyl chloromethyl ether

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311+H331-H318-H341-H373-H402-H411
Precautionary Statements:P201-P280-P301+P330+P331-P303+P361+P353-P305+P351+P338
Class:8(6.1)
UN#:2922
Packing Group:

Application In Synthesis of Benzyl chloromethyl ether

* 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 [ 3587-60-8 ]

[ 3587-60-8 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 3587-60-8 ]
  • [ 108290-86-4 ]
  • [ 108290-88-6 ]
  • 3
  • [ 3587-60-8 ]
  • [ 15965-57-8 ]
  • 1-benzyloxymethyl-2-chloro-4-methylbenzimidazole [ No CAS ]
  • 1-benzyloxymethyl-2-chloro-7-methylbenzimidazole [ No CAS ]
  • 4
  • [ 3587-60-8 ]
  • [ 161117-83-5 ]
  • 4-(Benzyloxymethyl)-2-methoxy-3-pyridinecarbamic acid 1,1-dimethylethyl ester [ No CAS ]
  • 5
  • [ 3587-60-8 ]
  • [ 117976-90-6 ]
  • [ 184713-27-7 ]
  • 6
  • [ 3587-60-8 ]
  • [ 5451-55-8 ]
  • 1-benzyloxymethyl-4-<i>tert</i>-butyl-cyclohexanecarboxylic acid [ No CAS ]
  • 7
  • [ 3587-60-8 ]
  • [ 2150-46-1 ]
  • [ 512165-74-1 ]
  • 8
  • [ 3587-60-8 ]
  • [ 10323-39-4 ]
  • 1-[(benzyloxy)methoxy]-4-bromo-2-(tert-butyl)benzene [ No CAS ]
  • 9
  • [ 705280-65-5 ]
  • [ 3587-60-8 ]
  • [ 872182-65-5 ]
  • 10
  • [ 3587-60-8 ]
  • [ 20901-53-5 ]
  • [ 896141-17-6 ]
  • 11
  • [ 3587-60-8 ]
  • [ 1233494-98-8 ]
  • 12
  • [ 3587-60-8 ]
  • [ 7126-57-0 ]
  • ethyl 1-(benzyloxymethyl)-4-folmyl-1H-pyrrole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% To an ice-cooled solution of 4 (4.1 g, 24.5 mmol) in dry THF (163 mL), t-BuOK(4.12 g, 36.75 mmol) was added and the mixture was stirred under argon atmosphere for 15 min. Then, 18-Crown-6 (647 mg, 2.45 mmol) was added and the whole mixture was stirred for additional 15 min at 0 C. A solution of benzyloxymethyl chloride (8.5 mL, 36.75 mmol) in dry THF (18.2 mL) was added dropwise. After completion of the addition, the mixture was stirred for 30 min at 0 C under argon atmosphere. The solvent was removed under reduced pressure, the crude residue was dissolved in DCM and extracted with H2O. The aqueous layer was backwashed with DCM (3×). The combined organic layers were washed with brine (1×), dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The oily residue was purified by silica gel flash column chromatography (n-hexane/EtOAc 95:5) to afford 5 (~6 g, 85 %) as a beige oil. Rf (n-hexane/EtOAc 6:4) 0.49.IR (KBr): max 1714, 1682, 1234, 1190, 1128, 517 cm-1. 1H NMR (CDCl3, 400 MHz): 9.76 (s, 1H), 7.55 (d, J = 1.8 Hz, 1H), 7.37 (d, J =1.8 Hz, 1H), 7.33-7.22 (m, 5H), 5.76 (s, 2H), 4.52 (s, 2H), 4.28 (q, J = 7.1 Hz,2H), 1.33 (t, J = 7.1 Hz, 3H). 13C NMR (CDCl3, 100 MHz): 185.36, 160.71, 136.67, 133.04, 128.71 (2×C),128.29, 128.11, 127.93 (2×C), 125.53, 124.90, 117.81, 77.56, 71.18, 60.89,14.39. MS (ESI+) (m/z): 310.25 [M+Na]+. HRMS-ESI (m/z): [M+Na]+ calcd for C16H17NO4: 310.10498, found: 310.10516.
  • 13
  • [ 213767-09-0 ]
  • [ 3587-60-8 ]
  • [ 2605-68-7 ]
  • (4R,5S,E)-methyl 6-((benzyloxy)methoxy)-4,5-dihydroxy-2-methylhex-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Sodium hydroxideaq. (2 M, 85 mL, 170mmol) was added to a solution ofcarbomethoxy methyl triphenylphosphonium bromide (5.15 g,12.0mmol) and CH2Cl2 (20 mL) at room temperature. Afterstirring for 15min at room temperature, the solution wasextracted with CHCl3 (2 15 mL), washed with brine (15 mL),dried over Na2SO4 and concentrated. The resulting ylide wasused without further purification.A solution of the ylide and CH2Cl2 (30 mL) was added to asolution of lactol 36 (1.00 g, 5.98mmol) and CH2Cl2 (30 mL) atroom temperature. After maintaining for 19 h at room temperature,diisopropylethylamine (5.2 mL, 30mmol) and BOMCl(3.3 mL, 24mmol) were added to the yellow solution at roomtemperature. The solution was maintained for 2 d at roomtemperature, quenched with H2O (40 mL) and extracted withCHCl3 (3 30 mL). The combined organic extracts werewashed with brine (30 mL), dried over Na2SO4 and concentrated.The residue was purified by silica gel column chromatography(EtOAc/hexane 1:24 to 1:7) to give 2.27 g of a mixtureof the unsaturated methylester 37 and benzyl alcohol, whichwas used in the next step without further purification. Foran analytical sample, the mixture was purified by HPLC(PEGASIL Silica 1205250 20 mm, UV 254 nm, EtOAc/hexane 1:3, 10mL/min, TR = 12min) to afford the pureunsaturated methylester 37: a colorless oil; [α]24D 6.5 (c 1.06,CHCl3); IR (film) 2988, 2936, 2885, 1719, 1248, 1048, 1028cm1; 1HNMR (500 MHz, CDCl3) δ 7.367.27(m, 5H), 6.69(dq, J = 8.9, 1.7 Hz, 1H), 4.98 (dd, J = 8.9, 6.6 Hz, 1H), 4.77(d, J = 8.1 Hz, 1H), 4.75 (d, J = 8.1 Hz, 1H), 4.60 (d, J = 14.9Hz, 1H), 4.58 (d, J = 14.9 Hz, 1H), 4.42 (ddd, J = 7.5, 6.6,4.6 Hz, 1H), 3.72 (s, 3H), 3.57 (dd, J = 10.6, 7.5 Hz, 1H), 3.51(dd, J = 10.6, 4.6 Hz, 1H), 1.90 (d, J = 1.7 Hz, 3H), 1.53(s, 3H), 1.41 (s, 3H); 13CNMR (125 MHz, CDCl3) δ 167.7 (C),137.8 (C), 136.4 (CH), 131.0 (C), 128.6 (CH), 128.0 (CH),127.9 (CH), 109.7 (C), 95.1 (CH2), 77.2 (CH), 73.9 (CH),69.7 (CH2), 67.2 (CH2), 52.2 (CH3), 28.0 (CH3), 25.5 (CH3),13.2 (CH3); HMRS (ESI) calcd for C19H26O6Na+ (M + Na)+373.1627, found 373.1618. A mixture of unsaturated methylester 37 (2.27 g) was dissolvedin AcOH/H2O (4:1, 20 mL) at room temperature. Thissolution was warmed to 40 C, and stirred for 1 d at 40 C. Thesolution was cooled to room temperature, and concentrated.Acetic acid and H2O were azeotropically removed from EtOH(4 40 mL) and toluene (20 mL) under reduced pressure. Theresidue was purified by silica gel column chromatography(EtOAc/hexane 3:1) to give 1.62 g of allylic vicinal diol 38(87%, 2 steps): a colorless oil; [α]27D +9.6 (c 1.16, CHCl3); IR(film) 3435, 2951, 2886, 1715, 1245, 1122, 1042, 750 cm1;1HNMR (500 MHz, CDCl3) δ 7.397.28(m, 5H), 6.71 (dd,J = 8.6, 1.5 Hz, 1H), 4.79 (d, J = 8.9 Hz, 1H), 4.78 (d, J = 8.9Hz, 1H), 4.64 (d, J = 12.1 Hz, 1H), 4.61 (d, J = 12.1 Hz, 1H),4.57 (ddd, J = 8.6, 5.2, 5.2 Hz, 1H), 3.82 (dddd, J = 6.3, 5.2,4.6, 3.8 Hz, 1H), 3.74 (s, 3H), 3.72 (dd, J = 10.6, 3.8 Hz, 1H),3.70 (dd, J = 10.6, 6.3 Hz, 1H), 3.02 (d, J = 4.6 Hz, 1H), 2.67(d, J = 5.2 Hz, 1H), 1.90 (d, J = 1.5 Hz, 3H); 13CNMR (125MHz, CDCl3) δ 168.1 (C), 138.7 (CH), 137.5 (C), 130.8 (C),128.6 (CH), 128.1 (CH), 128.0 (CH), 95.5 (CH2), 72.5 (CH),70.1 (CH2), 69.9 (CH), 69.7 (CH2), 52.2 (CH3), 13.3 (CH3);HMRS (ESI) calcd for C16H22O6Na+ (M + Na)+ 333.1314,found 333.1313.
  • 14
  • [ 213767-09-0 ]
  • [ 3587-60-8 ]
  • [ 2605-68-7 ]
  • C19H26O6 [ No CAS ]
  • [ 100-51-6 ]
YieldReaction ConditionsOperation in experiment
Sodium hydroxideaq. (2 M, 85 mL, 170mmol) was added to a solution ofcarbomethoxy methyl triphenylphosphonium bromide (5.15 g,12.0mmol) and CH2Cl2 (20 mL) at room temperature. Afterstirring for 15min at room temperature, the solution wasextracted with CHCl3 (2 15 mL), washed with brine (15 mL),dried over Na2SO4 and concentrated. The resulting ylide wasused without further purification.A solution of the ylide and CH2Cl2 (30 mL) was added to asolution of lactol 36 (1.00 g, 5.98mmol) and CH2Cl2 (30 mL) atroom temperature. After maintaining for 19 h at room temperature,diisopropylethylamine (5.2 mL, 30mmol) and BOMCl(3.3 mL, 24mmol) were added to the yellow solution at roomtemperature. The solution was maintained for 2 d at roomtemperature, quenched with H2O (40 mL) and extracted withCHCl3 (3 30 mL). The combined organic extracts werewashed with brine (30 mL), dried over Na2SO4 and concentrated.The residue was purified by silica gel column chromatography(EtOAc/hexane 1:24 to 1:7) to give 2.27 g of a mixtureof the unsaturated methylester 37 and benzyl alcohol, whichwas used in the next step without further purification. Foran analytical sample, the mixture was purified by HPLC(PEGASIL Silica 1205250 20 mm, UV 254 nm, EtOAc/hexane 1:3, 10mL/min, TR = 12min) to afford the pureunsaturated methylester 37: a colorless oil; [α]24D 6.5 (c 1.06,CHCl3); IR (film) 2988, 2936, 2885, 1719, 1248, 1048, 1028cm1; 1HNMR (500 MHz, CDCl3) δ 7.367.27(m, 5H), 6.69(dq, J = 8.9, 1.7 Hz, 1H), 4.98 (dd, J = 8.9, 6.6 Hz, 1H), 4.77(d, J = 8.1 Hz, 1H), 4.75 (d, J = 8.1 Hz, 1H), 4.60 (d, J = 14.9Hz, 1H), 4.58 (d, J = 14.9 Hz, 1H), 4.42 (ddd, J = 7.5, 6.6,4.6 Hz, 1H), 3.72 (s, 3H), 3.57 (dd, J = 10.6, 7.5 Hz, 1H), 3.51(dd, J = 10.6, 4.6 Hz, 1H), 1.90 (d, J = 1.7 Hz, 3H), 1.53(s, 3H), 1.41 (s, 3H); 13CNMR (125 MHz, CDCl3) δ 167.7 (C),137.8 (C), 136.4 (CH), 131.0 (C), 128.6 (CH), 128.0 (CH),127.9 (CH), 109.7 (C), 95.1 (CH2), 77.2 (CH), 73.9 (CH),69.7 (CH2), 67.2 (CH2), 52.2 (CH3), 28.0 (CH3), 25.5 (CH3),13.2 (CH3); HMRS (ESI) calcd for C19H26O6Na+ (M + Na)+373.1627, found 373.1618
 

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