4-Hydroxybenzoic Acid → Benzoic acid, 4-(benzoyloxy)-

HRID 854222Notes

Reaction equation

HRID 854222 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.[OH-].[Na+].Cl>O.CC(C)=O>[C:1]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 119979Benzoic acid, 4-(benzoyloxy)-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

17.3 ml (20.90 g, 149 mmol) of benzoyl chloride (Aldrich, purity 99%) are added dropwise over a period of 30 minutes with vigorous stirring to an ice-cooled solution of 20.00 g (145 mmol) of 4-hydroxybenzoic acid (Aldrich, purity 99%) and 12.00 g (300 mmol) of sodium hydroxide in 300 ml of distilled water and 30 ml of acetone. After a further 30 minutes, the mixture is acidified using concentrated hydrochloric acid and diluted with 750 ml of distilled water. The resultant white precipitate is filtered off and recrystallized from methanol/ethanol/ethyl acetate (450 ml+225 ml+300 ml).

Workup

  1. filtrationThe resultant white precipitate is filtered off
  2. customrecrystallized from methanol/ethanol/ethyl acetate (450 ml+225 ml+300 ml)

Sources & evidence

ORD record
ord-9b2a0785085a4d2fa535ab1f670ecbaf
Source dataset
uspto-grants-2007_08
Patent number
US07258902B2

Reaction notes

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