Methanol → (4-Amino-3-nitrophenyl)(phenyl)methanol

HRID 1723126Notes

Reaction equation

HRID 1723126 reaction equation
[NH2:1][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+]>O>[NH2:1][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

5

Reactant 3

HCID 887MethanolHCID 5969704-Amino-3-nitrobenzophenoneHCID 4311764Sodium borohydride

Product 1

HCID 14518359(4-Amino-3-nitrophenyl)(phenyl)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(a-1) To a stirred and cooled (water-bath) mixture of 48.5 parts of (4-amino-3-nitrophenyl)phenylmethanone and 320 parts of methanol were added portionwise 11.4 parts of sodium tetrahydroborate. Upon completion, stirring was continued for 15 minutes at room temperature. 100 Parts of water were added and the methanol was evaporated. The precipitated product was filtered off, washed with water, dried, filtered and crystallized twice from a moisture of methanol and water, yielding 19.6 parts of 4-amino-3-nitro-α-phenylbenzenemethanol; mp. 125° C. (int. 124).

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. customthe methanol was evaporated
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customcrystallized twice from a moisture of methanol and water

Sources & evidence

ORD record
ord-4947ff887190423fa6c9feb318dc5047
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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