Ethanethiol → Methyl 1-(4-hydroxyphenyl)cyclopropane-1-carboxylate

HRID 17914Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]([O:14][CH3:15])=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.CCS.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:15][O:14][C:12]([C:9]1([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1)=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 1-(4-methoxyphenyl)cyclopropanecarboxylate (10.0 g, 48.5 mmol) in DCM (80 mL) was added EtSH (16 mL) under ice-water bath. The mixture was stirred at 0° C. for 20 min before AlCl3 (19.5 g, 0.15 mmol) was added slowly at 0° C. The mixture was stirred at 0° C. for 30 min. The reaction mixture was poured into ice-water, the organic layer was separated, and the aqueous phase was extracted with DCM (50 mL×3). The combined organic layers were washed with H2O, brine, dried over Na2SO4 and evaporated under vacuum to give 1-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester (8.9 g, 95%). 1H NMR (400 MHz, CDCl3) δ 7.20-7.17 (m, 2H), 6.75-6.72 (m, 2H), 5.56 (s, 1H), 3.63 (s, 3H), 1.60-1.57 (m, 2H), 1.17-1.15 (m, 2H).

Workup

additionwas added slowly at 0° C
customthe organic layer was separated
extractionthe aqueous phase was extracted with DCM (50 mL×3)
washThe combined organic layers were washed with H2O, brine
dry with materialdried over Na2SO4
customevaporated under vacuum

Sources & evidence

ORD record: ord-fc3837671c144020be731389226cb2d1
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741321B2

Reaction notes

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