Sodium Hydroxide → 2-[4-(4-Chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionic acid

HRID 973297Notes

Reaction equation

HRID 973297 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:29]=[CH:28][C:11]([CH2:12][O:13][C:14]([C:24]([F:27])([F:26])[F:25])([C:20]([F:23])([F:22])[F:21])[C:15]([O:17]CC)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][O:13][C:14]([C:20]([F:21])([F:22])[F:23])([C:24]([F:25])([F:26])[F:27])[C:15]([OH:17])=[O:16])=[CH:28][CH:29]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13384260Ethyl 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionate

Product 1

HCID 133842612-[4-(4-Chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionate (3.3 g.), N aqueous sodium hydroxide (15 ml.) and ethanol (80 ml.) is stirred at ambient temperature for 18 hours, filtered, and the filtrate is evaporated in vacuo. An aqueous suspension of the residual solid is acidified with concentrated hydrochloric acid. The solid is filtered off, washed with water, dried and crystallised from cyclohexane to give 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionic acid, m.p. 130°-33° C. (2.5 g.)

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated in vacuo
  3. additionAn aqueous suspension of the residual solid
  4. filtrationThe solid is filtered off
  5. washwashed with water
  6. customdried
  7. customcrystallised from cyclohexane

Sources & evidence

ORD record
ord-979fb5bae94f4ddeb2cca1df88c7b923
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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