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

HRID 1058394Notes

Reaction equation

HRID 1058394 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-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoic acid, methyl ester (Example 94; 2.1 g, 6.6 mmol) and 1N 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). 1N hydrochloric acid solution (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 crystallized from ether/hexane to afford 2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoic acid (1.59 g, 79% yield) as an off-white solid.

Workup

  1. filtrationThe solution was filtered through Celite
  2. washthe filter cake was washed with water (5 mL)
  3. addition1N hydrochloric acid solution (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. customcrystallized from ether/hexane

Sources & evidence

ORD record
ord-fbb4f94e758b442fb3680793d196963e
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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