Methanol → Methyl 4-Iodophenylacetate

HRID 270934

Reaction equation

HRID 270934 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-f7d5cee144ee476c8bae7139ebf4f257
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Linked notes

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