Sulfuric Acid → 1-(2-Ethyl-butyl)-cyclohexanecarboxylic acid

HRID 656711Notes

Reaction equation

C([O:5][C:6]([C:8]1([CH2:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])(C)(C)C.OS(O)(=O)=O>CC(O)=O>[CH2:18]([CH:15]([CH2:16][CH3:17])[CH2:14][C:8]1([C:6]([OH:7])=[O:5])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[CH3:19]

Participants

Conditions

Temperature: 95 °C

Procedure

To a stirred solution of 1-(2-Ethyl-butyl)-cyclohexanecarboxylic acid t-butyl ester (2.0 g, 7.45 mmol) in AcOH (6 mL) 4M H2SO4 (0.6 mL, 2.4 mmol) was added dropwise at 95° C. After 18 h at this temperature, another portion of AcOH (4 mL) and 4M H2SO4 (0.6 mL, 2.4 mmol) was added and stirring at 95° C. was continued for 4 h. Then the reaction was complete according to GC. The reaction mixture was concentrated and then worked up by extraction to afford 1.4 g (88%) 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid, purity 99% (GC area).

Workup

waitwas continued for 4 h
concentrationThe reaction mixture was concentrated
extractionworked up by extraction

Sources & evidence

ORD record: ord-f767a2cfbed544dbbe10940bbc7874b1
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071803B2

Reaction notes

Loading…