Acetic Anhydride → HCID 19736808, compound

HRID 326394Notes

Reaction equation

[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[C:8]([C:16]1[CH:17]=[C:18]([CH:22]=CC=1O)[C:19]([OH:21])=[O:20])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>O>[C:8]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:6][C:5]=1[O:4][C:1](=[O:3])[CH3:2])[C:19]([OH:21])=[O:20])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 8 °C

Procedure

Acetic anhydride (10.5 g, 0.103 mmol) was added to a solution of 3-benzoyl-4-hydroxybenzoic acid (12.5 g, 51.6 mole) and NaOH (4.33 g, 0.108 mmol) in 250 ml of water under nitrogen. The clear colorless solution was stirred at 8° C. for one hour. The product separated initially as a colorless oil which soon crystallized to a white solid. The slurry was made strongly acidic by adding concentrated HCl, and was extracted with ether. The ether extract was washed with water, and dried with MgSO4 and evaporated to dryness providing crude acetoxy acid. The crude product was recrystallized from a mixture of 200 ml of toluene and 150 ml of cyclohexane to give 3-benzoyl-4-acetoxybenzoic acid with a m.p. of 162.5° C. to 163° C.

Workup

customThe product separated initially as a colorless oil which
customsoon crystallized to a white solid
additionby adding concentrated HCl
extractionwas extracted with ether
extractionThe ether extract
washwas washed with water
dry with materialdried with MgSO4
customevaporated to dryness
customproviding crude acetoxy acid
customThe crude product was recrystallized from a mixture of 200 ml of toluene and 150 ml of cyclohexane

Sources & evidence

ORD record: ord-ad6deef5771d4179aaa5a5ee5a9c9200
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05268443

Reaction notes

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