Acetic Anhydride → 2-(1,3-Benzodioxol-5-yl)ethyl acetate

HRID 1251827

Reaction equation

[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10](O)[CH3:11])=[CH:4][C:3]=2[O:2]1.[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:16][CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2-(3,4-methylenedioxy)phenyl-1-ethanol (1.68 g, 10 mmol) in dry pyridine was added acetic anhydride and the resultant reaction mixture was stirred at 80° C. for 1 h. The reaction mixture was poured into ice-water and was extracted with ether (2×75 ml). The combined ether extract was washed with water (2×50 ml), 5% Hcl (2×50 ml) and then with 5% NaHCO3 (2×50 ml). The organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure to give 1-acetoxy-2-[(3,4-methylenedioxy)phenyl]ethane as a solid (1.7 g, 81% yield).

Workup

customthe resultant reaction mixture
extractionwas extracted with ether (2×75 ml)
extractionThe combined ether extract
washwas washed with water (2×50 ml), 5% Hcl (2×50 ml)
dry with materialThe organic layer was dried over magnesium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-ad856a2cdaca4eeaa26f8226187a2e8c
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06342610B2

Linked notes

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