Hydrochloric Acid → 4,4'-Dichlorobenzhydrol

HRID 249166

Reaction equation

HRID 249166 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>C(O)(C)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70344,4'-DichlorobenzophenoneHCID 4311764Sodium borohydride

Product 1

HCID 70334,4'-DichlorobenzhydrolYield 98.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4,4'-dichlorobenzophenone (2.51 g) in isopropyl alcohol (15 ml) was added sodium borohydride (0.45 g). The mixture was stirred for 4 hours at 50° C. and poured into diluted hydrochloric acid (60 ml). The organic layer was extracted with ethyl acetate (20 ml) and washed with water (30 ml×2). The solution was dried over magnesium sulfate. The solvent was removed in vacuo to give colorless oil of bis(4-chlorophenyl)methanol (2.50 g).

Workup

  1. extractionThe organic layer was extracted with ethyl acetate (20 ml)
  2. washwashed with water (30 ml×2)
  3. dry with materialThe solution was dried over magnesium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1992318223c54782a559e8236f189c69
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Linked notes

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