Water → 4-(Trifluoromethyl)benzenesulfonic acid 3-acetoxy-3-methylbutyl ester

HRID 1886752Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][CH2:13][CH2:14][C:15]([OH:18])([CH3:17])[CH3:16])(=[O:11])=[O:10])=[CH:5][CH:4]=1.O.[C:22](Cl)(=[O:24])[CH3:23]>C(Cl)Cl>[C:22]([O:18][C:15]([CH3:16])([CH2:14][CH2:13][O:12][S:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:8][CH:7]=1)(=[O:11])=[O:10])[CH3:17])(=[O:24])[CH3:23]

Participants

Conditions

Temperature: 20 °C

Procedure

To a mixture of the alcohol 4 (0.500 g, 1.6 mmol), ZrOCl28.H2O (0.0025 g, 0.5 mol %) in methylene chloride (5 mL), acetyl chloride (0.251 g, 3.2 mmol) is added and the reaction is stirred for overnight at 20° C. The reaction on completion, is diluted with methylene chloride (5 mL) and washed with saturated sodium bicarbonate (2×10 mL), brine (1×10 mL) and dried. The solvent is evaporated to get the crude product. 1H NMR (400 MHz, CDCl3) δ1.56 (d, J=8.0, 6H), 1.60 (d, J=8.0, 5H), 2.14 (t, J=6.8, 2H), 4.33 (t, J=6.8, 2H), 7.82 (d, J=8.1, 2H), 8.04 (d, J=8.0, 2H).

Workup

customThe reaction on completion
washwashed with saturated sodium bicarbonate (2×10 mL), brine (1×10 mL)
customdried
customThe solvent is evaporated

Sources & evidence

ORD record: ord-66f0be8a2789493489a80884e4f85a41
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501382B1

Reaction notes

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