Acetic Acid → 5-(Benzyloxy)-2-(methoxycarbonyl)-1-tetralone

HRID 1271265Notes

Reaction equation

[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][CH2:21][C:22]2=[O:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(=O)C>O1CCOCC1.O>[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][CH:21]([C:3]([O:6][CH3:7])=[O:8])[C:22]2=[O:27])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 82.5 °C

Procedure

Under an argon atmosphere, 2.09 g of 60% sodium hydride was suspended in 30 ml of anhydrous dioxane and 11.51 g of dimethyl carbonate was added. While stirring with heating in an oil bath at 80 to 85° C., a solution of 6.58 g of 5-(benzyloxy)-1-tetralone in 15 ml of dioxane was added dropwise over about one hour. After stirring for one hour, the reaction solution was ice-cooled and 52 ml of an aqueous 1N acetic acid solution was added dropwise. The reaction solution was diluted with water, extracted with diethyl ether, washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.95 g of the desired compound as a pale yellow oily substance.

Workup

stirringAfter stirring for one hour
temperaturecooled
extractionextracted with diethyl ether
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-435f2a26a0204e24ab77c276ef29e0fd
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07205302B2

Reaction notes

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