Isopropanol → 4-Chloro-3-hydroxy-benzoic acid isopropyl ester

HRID 1271648

Reaction equation

HRID 1271648 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].[CH:12](O)([CH3:14])[CH3:13]>>[CH:12]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([OH:11])[CH:4]=1)([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 3776IsopropanolHCID 1418724-Chloro-3-hydroxybenzoic acid

Product 1

HCID 694189894-Chloro-3-hydroxy-benzoic acid isopropyl esterYield 75%

Conditions

Temperature
85 °C

Procedure

4-Chloro-3-hydroxy-benzoic acid (100 mg, 0.58 mmol) and 1 mL of isopropanol were mixed and then heated to 85° C. for overnight. The mixture was then concentrated in vacuum and the resulting residue was purified by flash chromatography (8–20% EtOAc/Hex) to give the desired ester (94 mg, 75%). MS (DCI) m/z 215 (M+H)+, 232 (M+NH4)+.

Workup

  1. concentrationThe mixture was then concentrated in vacuum
  2. customthe resulting residue was purified by flash chromatography (8–20% EtOAc/Hex)

Sources & evidence

ORD record
ord-d160994da4dc4be5bb9d588354b12d3d
Source dataset
uspto-grants-2007_04
Patent number
US07205409B2

Linked notes

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