Acetone → Methyl 4-(2-hydroxypropan-2-yl)benzoate

HRID 855296Notes

Reaction equation

C([Mg]Cl)(C)C.I[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1.[CH3:17][C:18]([CH3:20])=[O:19]>C1COCC1>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:15]=[CH:16][C:7]([C:18]([OH:19])([CH3:20])[CH3:17])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: -20 °C

Procedure

6.3 ml of a 2 molar solution of isopropylmagnesium chloride in THF (12 mmol) were added dropwise to a solution of 3 g methyl 4-iodobenzoate (11.5 mmol) in 30 ml THF at a temperature of −20° C. The reaction mixture was stirred for 1.5 h at −20° C., then 1.26 ml acetone (17 mmol) were added and the mixture was allowed to warm to rt. After 30 min at ambient temperature the reaction was quenched with methanol, poured into water and extracted with EtOAc. The combined extracts were washed with brine, dried with magnesium sulfate, filtered and concentrated. Chromatographic purification (silica gel; c-hexane/EtOAc 2:1) of the remaining residue yielded 1.64 g (74%) of 4-(1-hydroxy-1-methyl-ethyl)-benzoic acid methyl ester as a colorless liquid. 1H-NMR (CDCl3, 300 MHz): δ 1.60 (s, 6H), 3.91 (s, 3H), 7.56 (d, J=9 Hz, 1H), 8.01 (d, J=9 Hz, 1H).

Workup

temperatureto warm to rt
customAfter 30 min at ambient temperature the reaction was quenched with methanol
additionpoured into water
extractionextracted with EtOAc
washThe combined extracts were washed with brine
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated
customChromatographic purification (silica gel; c-hexane/EtOAc 2:1) of the remaining residue

Sources & evidence

ORD record: ord-83dcde08e4e947499ed5ce30a49d1fd7
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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