Hydrochloric Acid → 4-Amino-alpha-methylbenzenemethanol

HRID 1758220Notes

Reaction equation

HRID 1758220 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=1)([O-])=O.Cl>C(O)C>[NH2:3][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([OH:14])[CH3:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7487p-NitroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 857534-Amino-alpha-methylbenzenemethanolYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under nitrogen, 2.85 g (75 mmol) sodium borohydride, 500 mg (0.9 mmol) cobalt (II) phthalocyanine and 1.65 g (10 mmol) p-nitro acetophenone are agitated in 50 ml ethanol for 48 hours at 20° C. The reaction mixture is acidified with 5N hydrochloric acid, cooling with ice, and the blue precipitate is centrifuged which is washed with methanol. The centrifugate collected is concentrated and the residue separated into water and ether. The water phase is alkalized with sodium hydroxide and extraction is accomplished with ether. The ether phase is dried with sodium sulfate and concentrated, leaving behind 1.08 g (79%) α-(p-aminophenyl)-ethanol.

Workup

  1. temperaturecooling with ice
  2. washis washed with methanol
  3. customThe centrifugate collected
  4. concentrationis concentrated
  5. customthe residue separated into water and ether
  6. extractionThe water phase is alkalized with sodium hydroxide and extraction
  7. dry with materialThe ether phase is dried with sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0eb3f51cb7ca41d484795720b517e143
Source dataset
uspto-grants-1983_02
Patent number
US04372893

Reaction notes

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