Tetrahydrofuran → 1-(3-Tert-butyl-phenyl)-3-methylene-cyclohexanecarboxylic acid

HRID 132101Notes

Reaction equation

HRID 132101 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C[Si](C)(C)CC[O:28][C:29]([C:31]1([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([CH3:47])([CH3:46])[CH3:45])[CH:39]=2)[CH2:36][CH2:35][CH2:34][C:33](=[CH2:37])[CH2:32]1)=[O:30]>>[C:44]([C:40]1[CH:39]=[C:38]([C:31]2([C:29]([OH:30])=[O:28])[CH2:36][CH2:35][CH2:34][C:33](=[CH2:37])[CH2:32]2)[CH:43]=[CH:42][CH:41]=1)([CH3:47])([CH3:45])[CH3:46]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 597337701-(3-Tert-butyl-phenyl)-3-methylene-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester

Product 1

HCID 597337311-(3-Tert-butyl-phenyl)-3-methylene-cyclohexanecarboxylic acidYield 107.2%

Procedure

A 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (15.0 mL, 15.0 mmol) was added to 1-(3-tert-butyl-phenyl)-3-methylene-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester (2.67 mg, 7.16 mmol). After stirring for 16 h, the solution was concentrated, diluted with 10% aqueous hydrochloric acid, and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to yield 2.09 g (100% yield) of 1-(3-tert-butyl-phenyl)-3-methylene-cyclohexanecarboxylic acid as a yellow oil.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with 10% aqueous hydrochloric acid
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-89e0d65b0b0a4531a37e2452c69aba3f
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Reaction notes

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