Sulfuric Acid → 3-(2'-Chloro-4'-trifluoromethylphenoxy)-benzyl alcohol

HRID 1252649Notes

Reaction equation

HRID 1252649 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9].COCCOC.[BH4-].[Na+].S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:16]=[C:15]([C:17]([F:18])([F:20])[F:19])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][OH:9]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 80711,2-Dimethoxyethane2×HCID 4311764Sodium borohydrideHCID 13090780HCID 13090780, compound

Product 1

HCID 130906883-(2'-Chloro-4'-trifluoromethylphenoxy)-benzyl alcoholYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 90 parts by weight of 3-(2'-chloro-4'-trifluoromethylphenoxy)-benzaldehyde in 300 parts by volume of ethylene glycol dimethyl ether was added dropwise to a suspension of 5.7 parts by weight of sodium borohydride in 200 parts by volume of ethylene glycol dimethyl ether at 0° C. The reaction mixture was further stirred for 12 hours at room temperature, 500 parts by volume of water were added and the mixture was acidified with 10% strength sulfuric acid. It was then extracted with ether, the organic phase was dried with magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. Fractional distillation of the residue gave 80 parts by weight (89% of theory) of 3-(2'-chloro-4'-trifluoromethylphenoxy)-benzyl alcohol (compound No. 3) of boiling point 140°-145° C./0.1 bar and refractive index nD25 : 1.5330.

Workup

  1. extractionIt was then extracted with ether
  2. dry with materialthe organic phase was dried with magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. distillationFractional distillation of the residue

Sources & evidence

ORD record
ord-0316f30f244b406c9d1a7e915ddcd89d
Source dataset
uspto-grants-1988_05
Patent number
US04744812

Reaction notes

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