Hydrochloric Acid → HCID 53898321, compound

HRID 1413866Notes

Reaction equation

HRID 1413866 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([N+:24]([O-:26])=[O:25])[C:7]([OH:23])=[C:8]([C:10]([C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[C:13]=2[OH:22])=[O:11])[CH:9]=1.Cl>C(O)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([N+:24]([O-:26])=[O:25])[C:7]([OH:23])=[C:8]([CH:10]([OH:11])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[C:13]=2[OH:22])[CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20291111HCID 20291111, compound

Product 1

HCID 53898321HCID 53898321, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (3.5 g) was added portionwise to a stirred solution of bis(5-chloro-2-hydroxy-3-nitrophenyl) ketone (10 g) in ethanol (150 ml) the solution being maintained at a temperature of 0° C. On completion of the addition the temperature of the solution was allowed to rise to ambient temperature and the mixture was stirred overnight at ambient temperature. The solution was diluted with water, acidified with hydrochloric acid and the product extracted into ethyl acetate. The solvent was removed by distillation under reduced pressure to give bis-(5-chloro-2-hydroxy-3-nitrophenyl)methyl alcohol (9.0 g) which on recrystallisation from ethanol/hexane had a melting point of 180° C.

Workup

  1. additionOn completion of the addition the temperature of the solution
  2. customto rise to ambient temperature
  3. extractionthe product extracted into ethyl acetate
  4. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a400377dd45f4d73989f1e5dba307597
Source dataset
uspto-grants-1981_02
Patent number
US04251546

Reaction notes

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