4-Toluenesulfonyl chloride → 2-Tert-butyl-6-chlorocyclohexanone

HRID 12022

Reaction equation

C(NC(C)C)(C)C.[C:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:18])([CH3:11])([CH3:10])[CH3:9].C1(C)C=CC(S([Cl:28])(=O)=O)=CC=1>O1CCCC1>[C:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([Cl:28])[C:13]1=[O:18])([CH3:11])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: -78 °C

Procedure

N-butyl lithium is added dropwise to a solution, cooled to 0° C., of diisopropylamine (5.5 mmol) in dry tetrahydrofuran. After the addition is complete the mixture is cooled to −78° C., and a solution of 2-tert-butylcyclohexanone (5 mmol) in dry tetrahydrofuran (50 ml) is introduced, followed by the addition of p-toluenesulphonyl chloride (5 mmol), also dissolved in dry tetrahydrofuran (50 ml). The reaction mixture is heated to room temperature and after stirring for 30 mins over silica gel filtered with ether as eluant. After concentration by evaporation in a vacuum 2-tert-butyl-6-chlorcyclohexanone (760 mg) is obtained in a yield of 81% (Tet. Lett. 1999, 40(12), 2231-2234).

Workup

additionAfter the addition
temperatureThe reaction mixture is heated to room temperature
filtrationfiltered with ether as eluant
concentrationAfter concentration
customby evaporation in a vacuum 2-tert-butyl-6-chlorcyclohexanone (760 mg)
customis obtained in a yield of 81% (Tet. Lett. 1999, 40(12), 2231-2234)

Sources & evidence

ORD record: ord-2490bc6217a344258faf2fe00e97dd10
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727979B2

Linked notes

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