Sulfuric Acid → 4'-Chloro-2-hydroxymethylbenzhydrol

HRID 257764Notes

Reaction equation

HRID 257764 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](O)=[O:11])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O>CO>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]([C:8]2[C:9]([CH2:10][OH:11])=[CH:13][CH:14]=[CH:15][CH:16]=2)[OH:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 665642-(4'-Chlorobenzoyl)benzoic acid

Product 1

HCID 197815594'-Chloro-2-hydroxymethylbenzhydrol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 55 g (0.3M) of 2-(4-chlorobenzoyl) benzoic acid, 5 ml of concentrated sulphuric acid and 500 ml of methanol was heated under reflux for 3 hours. The mixture was evaporated and the residue was taken up in dichloromethane washed with water then aqueous sodium bicarbonate. The dichloromethane was dried and evaporated. The residue was then reduced with lithium aluminium hydride in an analogous manner to that described in Example X1 to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe mixture was evaporated
  4. washwashed with water
  5. dry with materialThe dichloromethane was dried
  6. customevaporated

Sources & evidence

ORD record
ord-dff5d578cf57474aa66ef86101b5313c
Source dataset
uspto-grants-1993_11
Patent number
US05264436

Reaction notes

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