Methanol → HCID 13384277, compound

HRID 973305Notes

Reaction equation

HRID 973305 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][O:13][C:14]([CH3:23])([C:19]([F:22])([F:21])[F:20])[C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[K+].CO>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][O:13][C:14]([CH3:23])([C:19]([F:20])([F:21])[F:22])[C:15]([OH:17])=[O:16])=[CH:24][CH:25]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 13384276HCID 13384276, compound

Product 1

HCID 13384277HCID 13384277, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the impure ester fraction from the previous example (fraction A) of (±)-methyl 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-methylpropionate (15.7 g.), potassium hydroxide (3.0 g.), methanol (300 ml.) and water (30 ml.) is stirred at ambient temperature for 18 hours. The suspension is filtered, and the filtrate is evaporated. The residue is mixed with water, and the mixture is washed with ether. The aqueous phase is acidified with concentrated hydrochloric acid then extracted with ether. The extract is dried with sodium sulphate and evaporated. The residue is crystallised from cyclohexane and from a mixture of toluene and light petroleum (b.p. 60°-80° C.) to give (±)-2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-methylpropionic acid, m.p. 135°-136° C. (5.7 g.). The above process is repeated with (±)-methyl 2-(4-chloro-1-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionate obtained as an oil in Example 16, to give (±)-2-(4-chloro-1-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionic acid, m.p. 120°-121° C. (11.1 g.).

Workup

  1. filtrationThe suspension is filtered
  2. customthe filtrate is evaporated
  3. additionThe residue is mixed with water
  4. washthe mixture is washed with ether
  5. extractionthen extracted with ether
  6. dry with materialThe extract is dried with sodium sulphate
  7. customevaporated
  8. customThe residue is crystallised from cyclohexane and from a mixture of toluene and light petroleum (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-6db77de979464c338d51107cacb0073e
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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