4-Hydroxybenzoic Acid → 4-hydroxybenzoyl Chloride

HRID 1290324Notes

Reaction equation

HRID 1290324 reaction equation
[Cl-].[Cl:2]C1N(C)CC[NH+]1C.[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCCl>[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([Cl:2])=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic Acid2×HCID 8471TriethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride

Product 1

HCID 110519074-hydroxybenzoyl ChlorideYield 72%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To 9.72 g (0.0575 mole) of 2-chloro-1,3-dimethylimidazolinium chloride, 90 ml of 1,2-dichloroethane and 6.91 g (0.05 mole) of 4-hydroxybenzoic acid were added. To the mixture, 5.06 g (0.05 mole) of triethylamine was dropwise added over 30 minutes while maintaining the temperature of the mixture at 15°-20° C. Thereafter, the reaction was carried out at 15°-20° C. for 24 hours. The reaction mass was analyzed by gas chromatography and liquid chromatography. Unreacted 4-hydroxybenzoic acid remained 1.79 g (0.013 mole). 4-Hydroxybenzoyl chloride was obtained in the yield of 72%.

Workup

  1. temperaturewhile maintaining the temperature of the mixture at 15°-20° C

Sources & evidence

ORD record
ord-601a2238aaf0444b85ecee7a93e8b672
Source dataset
uspto-grants-1998_05
Patent number
US05750779

Reaction notes

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