Acetic Anhydride → HCID 13066702, compound

HRID 1163989Notes

Reaction equation

CO[C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:17][C:18]([OH:20])=[O:19].C(OC(=O)C)(=O)C>I>[C:11]1([CH3:16])[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][C:8]1[C:3]2[O:20][C:18](=[O:19])[CH2:17][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-[2-Methoxy-3-(o-tolyloxy)phenyl]acetic acid (34.0 g) was added to a mixture of acetic anhydride (50 ml) and 50% aqueous solution of hydrogen iodide (100 ml), and the mixture was refluxed under heating for an hour. The reaction mixture was poured into ice-water (1 l) and extracted with diethyl ether. The extract was washed with aqueous sodium hydrogen sulfite and water (twice) successively, dried over magnesium sulfate and then evaporated. The oily residue (34.0 g) was dissolved in acetic anhydride (50 ml), stirred at 100° C. for 1.5 hours and then evaporated. The crystalline residue (29.0 g) was recrystallized from methanol and diisopropyl ether successively to give colorless crystals of 7-(o-tolyloxy)-2,3-dihydrobenzofuran-2-one (22.0 g). mp 110°-111° C.

Workup

temperaturethe mixture was refluxed
temperatureunder heating for an hour
extractionextracted with diethyl ether
washThe extract was washed with aqueous sodium hydrogen sulfite and water (twice) successively,
dry with materialdried over magnesium sulfate
customevaporated
dissolutionThe oily residue (34.0 g) was dissolved in acetic anhydride (50 ml)
customevaporated
customThe crystalline residue (29.0 g) was recrystallized from methanol and diisopropyl ether successively

Sources & evidence

ORD record: ord-6c20e1885d084f3581ab52f59dbe6761
Source dataset: uspto-grants-1983_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04367238

Reaction notes

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