Methyl Acrylate → Methyl 3-(2-hydroxymethylphenylthio)propionate

HRID 481753

Reaction equation

HRID 481753 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12]>ClCCl.C(N(CC)CC)C>[OH:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[S:1][CH2:12][CH2:11][C:10]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 1382782-Mercaptobenzenemethanol

Product 1

HCID 19066905Methyl 3-(2-hydroxymethylphenylthio)propionateYield 87.1%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-mercaptobenzyl alcohol (1.00 g, 7.10 mmol) in dichloromethane (20 mL) at 0° C. was added methyl acrylate (0.70 mL, 7.70 mmol) followed by triethylamine (50 μL, 0.35 mmol). The mixture was allowed to warm to room temperature and stir for 4 h, at which point the solvent was removed with a rotary evaporator. The residue was subjected to column chromatography on silica gel (0-10% ethyl acetate in dichloromethane), affording 1.40 g (86%) of methyl 3-(2-hydroxymethylphenylthio)propionate. 1H NMR (CDCl3) δ 2.63 (t, 2, J=7), 3.18 (t, 2, J=7), 3.68 (s, 3), 4.79 (s, 2), 7.27 (m, 2), 7.43 (m, 2).

Workup

  1. customwas removed with a rotary evaporator

Sources & evidence

ORD record
ord-2e644bacc3834444a77064f2a39ce86a
Source dataset
uspto-grants-1998_08
Patent number
US05789584

Linked notes

Loading…