Diethyl Ether → [4-(Acetyloxy)-2-hydroxy-3-propylphenyl][2(acetyloxy)phenyl]methanone
Reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])=[O:13].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:37](OC(=O)C)(=[O:39])[CH3:38].[CH2:44]([O:46]CC)[CH3:45]>>[C:37]([O:11][C:6]1[CH:5]=[CH:4][C:3]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][C:44](=[O:46])[CH3:45])=[O:13])=[C:2]([OH:1])[C:7]=1[CH2:8][CH2:9][CH3:10])(=[O:39])[CH3:38]Participants
Procedure
Five grams of (2,4-dihydroxy-3-propylphenyl)- (2-hydroxyphenyl)methanone, 5.63 ml of triethylamine, and approximately 50 mg of dimethylaminopyridine were dissolved in 50 ml of diethyl ether at 0° C. Acetic anhydride (3.8 ml) was added dropwise. After stirring for 1 hour, the reaction mixture was partitioned between diethyl ether and water. The organic layer was separated, washed with 1N hydrochloric acid, a saturated solution of sodium bicarbonate, and a saturated solution of sodium chloride, dried over magnesium sulfate, and concentrated in vacuo. Purification by high pressure liquid chromatography over silica gel eluting with a 10-25% ethyl acetate in hexane gradient and concentration of the appropriate fractions provided 2.6 g of the desired title product as an oil.
Workup
- customthe reaction mixture was partitioned between diethyl ether and water
- customThe organic layer was separated
- washwashed with 1N hydrochloric acid
- dry with materiala saturated solution of sodium bicarbonate, and a saturated solution of sodium chloride, dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customPurification by high pressure liquid chromatography over silica gel eluting with a 10-25% ethyl acetate in hexane gradient and concentration of the appropriate fractions
Sources & evidence
- ORD record
- ord-b506f0a93f454478842c6ee5fb111de7
- Source dataset
- uspto-grants-1989_01
- Patent number
- US04801616
Reaction notes
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