1,1-Cyclopropanedimethanol 1-benzoate synthesis
- Product Name:1,1-Cyclopropanedimethanol 1-benzoate
- CAS Number:142148-11-6
- Molecular formula:C12H14O3
- Molecular Weight:206.24
Yield:142148-11-6 51%
Reaction Conditions:
with triethylamine in dichloromethane at 20;
Steps:
I.96.1 (1-(hydroxymethyl)cyclopropyl)methyl benzoate
21.89 g of cyclopropane- 1,1-diyldimethanol (0.214 mol) were dissolved in DCM (400 ml) and 29.8 ml triethylamine (1.0 eq.) was added. Then, 30.1 g of benzoyl chloride (1.0 eq.) was slowly added to the vigorously stirred mixture. The reaction temperature was adjusted to room temperature and stirring was continued overnight. The crude mixture was washed with saturated sodium bicarbonate solution, the organic layer was separated, dried with MgS04 and evaporated to dryness. The oily residue was purified by flash chromatography on silica with petrolether/ether. Monobenzoylated alcohol (1- (hydroxymethyl)cyclopropyl)methyl benzoate was obtained as a colorless oil (22.38 g, 51 %). LCMS (ESI+) m/z: [M+H]+ 207.10, [M+Na]+ 229.15 1H NMR (600 MHz, CDC13) δ ppm: 0.58 - 0.70 (m, 4H), 2.18 (s, 1H, OH), 3.53 (s, 2H), 4.32 (s, 2H), 7.42 - 7.49 (m, 2H), 7.55 - 7.60 (m, 1H), 8.04 - 8.09 (m, 2H).
References:
WO2017/50807,2017,A1 Location in patent:Page/Page column 197
39590-81-3
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