Ammonium Chloride → 2-(4-Fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl alcohol

HRID 325532Notes

Reaction equation

HRID 325532 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([CH:18]=[O:19])=[C:12]([CH3:17])[CH:13]=[C:14]([CH3:16])[CH:15]=2)=[CH:6][C:5]=1[CH3:20].[Cl-].[NH4+]>C(O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=2[CH2:18][OH:19])=[CH:6][C:5]=1[CH3:20]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 133169792-(4-Fluoro-3-methyl-phenyl)-4,6-dimethylbenzaldehyde

Product 1

HCID 133169802-(4-Fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.45 g, 12 mmoles) was added to a stirred suspension of 4'-fluoro-3,3',5-trimethyl-1,1'-biphenyl-2-carboxaldehyde (2.9 g, 12 mmoles) in ethanol (20 ml) which was cooled in an ice-water bath. After 5 minutes the cooling bath was removed and the reaction mixture was stirred at ambient temperature for one hour. The solution was cooled to 0° C. and excess ammonium chloride (2.67 g, 50 mmoles) was added and the mixture was partitioned between ether (150 ml) and water (50 ml). The water was separated and extracted with ether (50 ml). The combined ether extracts were washed with water (2×50 ml) dried (MgSO4), filtered, and the solvent evaporated in vacuo to leave the title compound, a gum which crystallized on standing, to give 2.77 g, m.p. 74°-75° C. A sublimed sample had m.p. 102°-103° C.

Workup

  1. temperaturewas cooled in an ice-water bath
  2. customAfter 5 minutes the cooling bath was removed
  3. temperatureThe solution was cooled to 0° C.
  4. customthe mixture was partitioned between ether (150 ml) and water (50 ml)
  5. customThe water was separated
  6. extractionextracted with ether (50 ml)
  7. washThe combined ether extracts were washed with water (2×50 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-9601c0e6f4cc4c87b97dc48c98f31690
Source dataset
uspto-grants-1984_04
Patent number
US04440927

Reaction notes

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