Sodium Hydroxide → 2-Chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acid

HRID 1352036Notes

Reaction equation

HRID 1352036 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:22])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:22])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 235607802-Chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acid, methyl ester

Product 1

HCID 226613772-Chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acidYield 79.1%

Procedure

A mixture of 2-chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acid, methyl ester (Example 19; 2.1 g, 6.6 mmol) and 1 M sodium hydroxide solution was stirred for 4 h at room temperature. The solution was filtered through Celite and the filter cake was washed with water (5 mL). 1 M HCl (22 mL) was added to the stirred filtrate and the resulting mixture was stirred for 2 h and then filtered. The solid was washed with water, dried and recrystallized from ether/hexane to give 2-chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acid (1.59 g, 79%) as an off-white solid.

Workup

  1. filtrationThe solution was filtered through Celite
  2. washthe filter cake was washed with water (5 mL)
  3. addition1 M HCl (22 mL) was added to the stirred filtrate
  4. stirringthe resulting mixture was stirred for 2 h
  5. filtrationfiltered
  6. washThe solid was washed with water
  7. customdried
  8. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-5d3c40c3d3c44720be4f2c90414446b9
Source dataset
uspto-grants-2007_05
Patent number
US07217728B2

Reaction notes

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