2,2,2-Trichloroethyl butyrate → 1-(4-(1-Ethoxyethoxy)phenyl)ethyl butyrate

HRID 344791Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To 120 ml of anhydrous diethyl ether was added 21 g (0.1 mole) of 1-(4-(1-ethoxyethoxy)phenyl)ethanol, 22.4 g (0.1 mole) of 2,2,2-trichloroethyl butyrate and 25.2 g of Lipase P (commercially available from Amano Seiyaku Kabushiki Kaisha) and the mixture was reacted with stirring at 25° C. for 90 hours. The reaction mixture was filtered by suction to remove Lipase P, the filtrate was concentrated and the concentrate was then purified by silica gel chromatography [ethyl acetate/n-hexane=1/4 by volume (hereinafter the same)] to give 9.6 g of S-form of 1-(4-(1-ethoxyethoxy)phenyl)ethanol (yield: 91%) and 13.0 g of R-form of 1-(4-(1-ethoxyethoxy)phenyl)ethyl butyrate (yield: 93%).

Workup

customwas reacted
filtrationThe reaction mixture was filtered by suction
customto remove Lipase P
concentrationthe filtrate was concentrated
customthe concentrate was then purified by silica gel chromatography [ethyl acetate/n-hexane=1/4 by volume (hereinafter the same)]

Sources & evidence

ORD record: ord-403b7bf7628e42c08eab167d228681af
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053507

Reaction notes

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