Acetic Acid → HCID 14990620, compound

HRID 2166042Notes

Reaction equation

HRID 2166042 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].CO.[BH4-].[Na+].C(O)(=O)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 14590583(4-Fluoro-3-nitrophenyl)(phenyl)methanone

Product 1

HCID 14990620HCID 14990620, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled (ice bath) solution of 24.5 parts of (4-fluoro-3-nitrophenyl) phenylmethanone in 120 parts of methanol were added portionwise 1.5 parts of sodium tetrahydroborate. Upon complete addition, stirring was continued for 15 minutes at 0° C. A solution of 3 parts of acetic acid in 25 parts of water was added dropwise to the mixture. Upon completion, the mixture was concentrated. Water was added to the residue and the product was extracted with dichloromethane. The extract was dried, filtered and concentrated, yielding 25.1 parts (100%) of 4-fluoro-3-nitro-α-phenylbenzenemethanol as an oily residue (int. 63).

Workup

  1. additionUpon complete addition
  2. concentrationUpon completion, the mixture was concentrated
  3. additionWater was added to the residue
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e7a3f7a9422c4786b95b933d29958c6e
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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