Hydrochloric Acid → 1-(1,3-Benzodioxol-5-yl)cyclobutanecarboxylic Acid

HRID 2110311Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:14]#N)[CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-:16].[K+].[OH2:18].Cl>C(O)CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:14]([OH:18])=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Conditions

Temperature: 180 °C

Procedure

1-Benzo[1,3]dioxol-5-yl-cyclobutanecarbonitrile (1.2 g) was slurried in ethylene glycol (10 mL) in a pressure tube and a large excess of KOH (1 g) was added. The tube was sealed and heated at 180° C. for 24 hours, cooled, poured into 100 mL of water, acidified with 1N HCl, extracted with ether, and the ether extracts were concentrated in vacuo and chromatographed on silica gel with an ethyl acetate:hexane:acetic acid mixture to give the desired 1-benzo[1,3]dioxol-5-yl-cyclobutanecarboxylic acid (850 mg, 65%). Data for this acid: MS 220 (M); 1H NMR (300 MHz, CDCl3): δ 11.4-11.8 (br. s, 1H), 2.78-6.85 (m, 3H), 5.95 (s, 2H) 2.75-2.85 (m, 2H), 2.40-2.55 (m, 2H), 1.8-2.2 (m, 2H); 13C NMR (75 MHz, CDCl3): δ 182.9, 147.9, 146.7, 137.2, 119.8, 108.2, 107.5, 101.3, 52.2, 32.6, 16.7.

Workup

customThe tube was sealed
temperaturecooled
extractionextracted with ether
concentrationthe ether extracts were concentrated in vacuo
customchromatographed on silica gel with an ethyl acetate

Sources & evidence

ORD record: ord-9bb0dd377fb54f008d01181a297b0403
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517892B2

Reaction notes

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