Potassium Carbonate → 3,5-Bis(trimethylsilyl)benzoic acid

HRID 613168Notes

Reaction equation

[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[OH-].[K+].[CH3:9][Si:10]([CH3:25])([CH3:24])[C:11]1[CH:12]=[C:13](C(=O)C)[CH:14]=[C:15]([Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:16]=1.S(=O)(O)[O-].[Na+]>O>[CH3:18][Si:17]([CH3:20])([CH3:19])[C:15]1[CH:14]=[C:13]([CH:12]=[C:11]([Si:10]([CH3:25])([CH3:24])[CH3:9])[CH:16]=1)[C:1]([OH:2])=[O:4]

Participants

Conditions

Temperature: 65 °C

Procedure

A suspension of 2.0 g (14 mmol) of Ca(OCl)2, 1.38 g (10 mmol) of potassium carbonate and 0.40 g (7.12 mmol) of potassium hydroxide in 40 ml of water was stirred at 65° C. for 30 minutes and filtered. The filtrate was added to 0.53 g (2 mmol) of 3',5'-bis(trimethylsilyl)acetophenone and the mixture was refluxed for 7.5 hours with stirring. After cooling, 3 ml of aqueous sodium bisulfite solution was added to the reaction mixture. The aqueous solution was extracted with AcOEt. The extract was washed successively with water and sat.aq.NaCl, dried over anhyd.Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel [eluent: n-hexane-AcOEt (2:1-1:1)] to give 0.27 g of white powder, m.p. >300° C. (yield 51%).

Workup

filtrationfiltered
temperaturethe mixture was refluxed for 7.5 hours
stirringwith stirring
temperatureAfter cooling
extractionThe aqueous solution was extracted with AcOEt
washThe extract was washed successively with water and sat.aq
dry with materialNaCl, dried over anhyd
customNa2SO4 and evaporated
customThe residue was purified by column chromatography on silica gel [eluent: n-hexane-AcOEt (2:1-1:1)]

Sources & evidence

ORD record: ord-d5589d8024b749bca777bbb17229f9b5
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE036477

Reaction notes

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