Benzene → HCID 15671128, compound
Reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].O[C:9]1[C:18](C)=[C:17]2[C:12]([C:13](=[O:32])[CH2:14][C:15]([CH3:31])([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[O:16]2)=[CH:11]C=1.N1C=CC=CC=1.C1C=CC=CC=1>O>[C:5]([O:4][C:1]1[C:18]([CH3:9])=[C:17]2[C:12]([C:13](=[O:32])[CH2:14][C:15]([CH3:31])([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[O:16]2)=[CH:11][CH:2]=1)(=[O:7])[CH3:6]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
3.3 g of acetic anhydride were added to a mixture of 9.3 g of 7-hydroxy-2,8-dimethyl-2-(4-nitrophenoxymethyl)-4-oxochroman (prepared as described in Preparation 16), 50 ml of pyridine and 50 ml of benzene and allowed to stand overnight. The reaction mixture was then poured into water and extracted with benzene. The benzene extract was washed with 5% w/v aqueous hydrochloric acid and then with water, after which it was dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was subjected to silica gel column chromatography eluted with a 20:1 by volume mixture of benzene and ethyl acetate, to obtain 9.7 g of the title compound as a pale yellow oily substance.
Workup
- extractionextracted with benzene
- extractionThe benzene extract
- washwas washed with 5% w/v aqueous hydrochloric acid
- dry with materialwith water, after which it was dried over anhydrous sodium sulfate
- distillationThe solvent was then distilled off under reduced pressure
- washeluted with a 20:1 by volume mixture of benzene and ethyl acetate
Sources & evidence
- ORD record
- ord-2ddf7602ac2f4c428e3ca31fc27561c4
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04873255
Reaction notes
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