Methanol → HCID 20314455, compound

HRID 2419909Notes

Reaction equation

HRID 2419909 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:30]=[CH:29][C:11]([O:12][CH2:13][O:14][C:15]([C:25]([F:28])([F:27])[F:26])([C:21]([F:24])([F:23])[F:22])[C:16]([O:18]CC)=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].CO>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][O:14][C:15]([C:21]([F:22])([F:23])[F:24])([C:25]([F:26])([F:27])[F:28])[C:16]([OH:18])=[O:17])=[CH:29][CH:30]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 961HydroxideHCID 20314448HCID 20314448, compound

Product 1

HCID 20314455HCID 20314455, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of ethyl 2-[4-(4-chlorophenyl)phenoxymethoxy]-3,3,3-trifluoro-2-trifluoromethylpropionate (502 mg.) postassium hydroxide (88 mg.), methanol (4 ml.) and water (1 ml.) is stirred at 20° C. for 22 hours, then evaporated in vacuo. The residue is dissolved in water, and the solution is acidified with 3 N-hydrochloric acid. The solid which separates is filtered off. Crystallisation from a mixture of cyclohexane and light petroleum (b.p. 40°-60° C.) gives prisms (204 mg.) of 2-[4-(4-chlorophenyl)phenoxymethoxy]-3,3,3-trifluoro-2-trifluoromethylpropionic acid, m.p. 134°-135° C.

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue is dissolved in water
  3. filtrationThe solid which separates is filtered off
  4. customCrystallisation
  5. additionfrom a mixture of cyclohexane and light petroleum (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-949d459a584e4b829218d90f43ae6415
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

Loading…