Sulfuric Acid → (1R,2S)-2-(4-Hydroxyphenyl)cyclopropanecarboxylic acid

HRID 922237Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@H:9]2[C:11](NC(C2C=CC=CC=2)CO)=[O:12])=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:24]>O1CCOCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:10][C@H:9]2[C:11]([OH:12])=[O:24])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 100 mL RB flask fitted with magnetic stirrer was charged with 22 mL of dioxan. To the stirred solvent were added (1R,2S)-2-(4-hydroxyphenyl)-N-(2-hydroxy-1-phenylethyl)cyclopropanecarboxamide (0.75 g, 2.52 mmol) and 3N sulfuric acid (22 mL). The reaction mixture was heated at 100° C. for 7 h. The reaction mixture was poured into ice and extracted with ethyl acetate (25 mL). The organic layer was washed with brine solution (25 mL). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as pale yellow oil (0.51 g, yield: 100%). 1H NMR (300 MHz, DMSO-d6): δ 12.20 (s, 1H), 9.25 (s, 1H), 6.93-6.96 (d, 2H), 6.64-6.67 (d, 2H), 2.24-2.31 (m, 1H), 1.63-1.68 (m, 1H), 1.31-1.37 (m, 1H), 1.20-1.26 (m, 1H).

Workup

customTo a 100 mL RB flask fitted with magnetic stirrer
additionThe reaction mixture was poured into ice
extractionextracted with ethyl acetate (25 mL)
washThe organic layer was washed with brine solution (25 mL)
dry with materialThe organic layer was dried over Na2SO4
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-47d98c3f3aea4f149de75bc221e2dddc
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278915B2

Reaction notes

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