Methanol → Methyl 4-Iodophenylacetate

HRID 460687

Reaction equation

HRID 460687 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1372144-Iodophenylacetic acid

Product 1

HCID 10378700Methyl 4-IodophenylacetateYield 86%

Procedure

A solution of 5 g (19 mmol) of (4-iodo-phenyl)-acetic acid in 50 mL of methanol (MeOH) was added dropwise 3.5 mL (48 mmol) of thionyl chloride (SOCl2), and the resulting mixture was stirred at rt for 36 h, after which time analysis by thin layer chromatography (TLC) indicated product formation. The mixture was concentrated to give 4.5 g (86% yield) of (4-iodo-phenyl)-acetic acid methyl ester as a pale beige oil as indicated by 1H NMR.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-f16e90a916704da2b92052ea9948e23b
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Linked notes

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