Benzyl Alcohol → 3-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid benzyl ester

HRID 709471Notes

Reaction equation

HRID 709471 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([C:14]1[CH:15]=[C:16]([CH2:21][CH:22]([O:26][CH2:27][CH3:28])[C:23]([OH:25])=[O:24])[CH:17]=[CH:18][C:19]=1[OH:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C=O)C.[CH2:34](O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[CH2:34]([O:24][C:23](=[O:25])[CH:22]([O:26][CH2:27][CH3:28])[CH2:21][C:16]1[CH:17]=[CH:18][C:19]([OH:20])=[C:14]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 65578Oxalyl chloride2×HCID 668649833-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid

Product 1

HCID 668645693-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid benzyl esterYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.364 g, 2.87 mmol) was added dropwise to a mixture of 3-(3-benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid (0.345 g, 1.15 mmol) and a catalytic amount of DMF in dry DCM (2.0 mL). The mixture was stirred for 17 h at room temperature before the excess oxalyl chloride was evaporated in vacuo. The remaining carboxylic acid chloride was redissolved in dry DCM (3.0 mL) and benzyl alcohol (0.15 g, 1.38 mmol) was added under nitrogen atmosphere. After stirring for 24 h at room temperature the solvent was removed in vacuo and the resulting oil was purified by column chromatography using DCM/MeOH (96:4) as the eluent to afford the title compound as an oil (0.22 g, 36.8%). Mass Spectrum: M−H+ 388.94.

Workup

  1. customwas evaporated in vacuo
  2. dissolutionThe remaining carboxylic acid chloride was redissolved in dry DCM (3.0 mL)
  3. customwas removed in vacuo
  4. customthe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-95c91a46e8884e5685929f8eb8049e78
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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