Hydrochloric Acid → 2,2,2-Trifluoro-1-(3-phenoxyphenyl)ethan-1-ol

HRID 1762643Notes

Reaction equation

HRID 1762643 reaction equation
[BH4-].[Na+].[O:3]([C:10]1[CH:11]=[C:12]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.O>CO>[F:18][C:17]([F:19])([F:20])[CH:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:11]=1)[OH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 199715852,2,2-Trifluoro-1-(3-phenoxyphenyl)ethanone

Product 1

HCID 142705712,2,2-Trifluoro-1-(3-phenoxyphenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.71 g of sodium borohydride were added in small fractions over 35 minutes at 0° C. to a solution of 56.1 g of the raw product of Step A in 235 ml of methanol and the mixture was stirred for 25 minutes while allowing the temperature to rise to room temperature. The mixture was added to aqueous 1N hydrochloric acid solution and water was added with stirring. The decanted aqueous phase was extracted with methylene chloride and the organic phase was washed with water and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with methylene chloride to obtain 13.3 g of (R, S) 2,2,2-trifluoro-1-(m-phenoxy-phenyl)-ethanol.

Workup

  1. customto rise to room temperature
  2. additionwas added
  3. stirringwith stirring
  4. extractionThe decanted aqueous phase was extracted with methylene chloride
  5. washthe organic phase was washed with water
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was chromatographed over silica gel
  8. washwas eluted with methylene chloride

Sources & evidence

ORD record
ord-adce006689fe407799ce1e39add16071
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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