Sodium Hydroxide → 5-Acetyl-2-isopropoxy-benzoic acid

HRID 1820816Notes

Reaction equation

C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[O:13][CH:14]([CH3:16])[CH3:15].[OH-].[Na+]>C1COCC1>[C:10]([C:8]1[CH:7]=[CH:6][C:5]([O:13][CH:14]([CH3:16])[CH3:15])=[C:4]([CH:9]=1)[C:3]([OH:17])=[O:2])(=[O:12])[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To 25.8 mmol 5-acetyl-2-isopropoxy-benzoic acid methyl ester in 100 ml THF was added 400 mmol 2 M aq NaOH, and the mixture was heated at 80° C. for 2 h. The mixture was then cooled to RT and extracted twice with ether. The aqueous phase was acidified with 15% aq hydrochloric acid and extracted 3 times with ethyl acetate. The combined organic phases were dried with Na2SO4. Evaporation in vacuo followed by trituration in ether afforded the title compound. MS (m/e): 221.2 ([M−H]−, 100%)

Workup

temperatureThe mixture was then cooled to RT
extractionextracted twice with ether
extractionextracted 3 times with ethyl acetate
dry with materialThe combined organic phases were dried with Na2SO4
customEvaporation in vacuo

Sources & evidence

ORD record: ord-9dc86f791ac4419089fdb51d3d426125
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605163B2

Reaction notes

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