Methanol → (4-Amino-3,5-dichlorophenyl)methanol

HRID 978474Notes

Reaction equation

HRID 978474 reaction equation
CO.C[O:4][C:5](=O)[C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([NH2:13])=[C:8]([Cl:14])[CH:7]=1.[BH4-].[Na+].C(O)(C)(C)C>O>[Cl:12][C:10]1[CH:11]=[C:6]([CH:7]=[C:8]([Cl:14])[C:9]=1[NH2:13])[CH2:5][OH:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 6386tert-ButanolHCID 604808Methyl 4-amino-3,5-dichlorobenzoateHCID 4311764Sodium borohydride

Product 1

HCID 13853668(4-Amino-3,5-dichlorophenyl)methanolYield 92.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanol (400 ml) was added dropwise over 2 hours to a mixture of methyl-3,5-dichloro-4-aminobenzoate (110 g), NaBH4 (142.5 g) and t-butanol (1.1 L). At the end of the addition, the mixture was refluxed 3 hours, cooled, then H2O (1.2 L) was carefully added. The resulting layers were separated and the organic phase was washed with H2O (2×200 mL), separated, dried (MgSO4), filtered and evaporated to afford the desired product (89 g), mp 110-112° C.

Workup

  1. additionAt the end of the addition
  2. temperaturethe mixture was refluxed 3 hours
  3. temperaturecooled
  4. customThe resulting layers were separated
  5. washthe organic phase was washed with H2O (2×200 mL)
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-4483cce3ec014637babad78c3de9e8e9
Source dataset
uspto-grants-1987_05
Patent number
US04665095

Reaction notes

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