Methanol → HCID 13384275, compound

HRID 2419935Notes

Reaction equation

HRID 2419935 reaction equation
[C:1]1([C:7]2[CH:24]=[CH:23][C:10]([CH2:11][O:12][C:13]([CH3:22])([C:18]([F:21])([F:20])[F:19])[C:14]([O:16]C)=[O:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].CO>O>[C:1]1([C:7]2[CH:24]=[CH:23][C:10]([CH2:11][O:12][C:13]([CH3:22])([C:18]([F:19])([F:20])[F:21])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 13384274HCID 13384274, compound

Product 1

HCID 13384275HCID 13384275, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (±)-methyl 2-[(4-phenyl)benzyloxy]-3,3,3-trifluoro-2-methylpropionate (28.1g.), potassium hydroxide (5.6g.), methanol (200ml.) and water (25ml.) is stirred at ambient temperature for 2.5 hours. The suspension is separated by filtration and the filtrate evaporated in vacuo. The residue is mixed with water, and the solution is washed with light petroleum (b.p. 60°-80° C). The aqueous phase is acidified with concentrated hydrochloric acid then extracted with ether. The extracts are dried (Na2SO4) and evaporated. The residue is crystallised from light petroleum (b.p. 80-100° C.) to give (±)-2-[(4-phenyl)benzyloxy]-3,3,3-trifluoro-2-methylpropionic acid (11.3g.), m.p. 132°-134° C.

Workup

  1. customThe suspension is separated by filtration
  2. customthe filtrate evaporated in vacuo
  3. additionThe residue is mixed with water
  4. washthe solution is washed with light petroleum (b.p. 60°-80° C)
  5. extractionthen extracted with ether
  6. dry with materialThe extracts are dried (Na2SO4)
  7. customevaporated
  8. customThe residue is crystallised from light petroleum (b.p. 80-100° C.)

Sources & evidence

ORD record
ord-df2dd07153fb4542ad3721f2fa5de3a9
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

Loading…