Acetic Acid → HCID 14990620, compound

HRID 2248321Notes

Reaction equation

HRID 2248321 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-08cbc4ea5ddb469fbd913c7d9558d967
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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