Cyclohexanol → HCID 19776117, compound

HRID 1612611Notes

Reaction equation

HRID 1612611 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:27])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].[Na+].[H][H].S(O[CH:37]1[CH2:42][CH2:41][CH:40]([CH2:43][CH2:44][CH2:45][CH2:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)CC1)(C)(=O)=O.[CH:53]1(O)CCCC[CH2:54]1.S(Cl)(C)(=O)=O.C(N(CC)CC)C>CS(C)=O.ClCCl>[CH2:40]([CH:43]1[CH2:44][CH2:45][CH:46]([CH:47]2[CH2:48][CH2:49][CH:50]([O:27][CH:14]([C:11]3[CH:10]=[CH:9][C:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:13][CH:12]=3)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:51][CH2:52]2)[CH2:54][CH2:53]1)[CH2:41][CH2:42][CH3:37]

Participants

9

Reactant 6

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 19776103HCID 19776103, compoundHCID 21666509HCID 21666509, compoundHCID 23325906HCID 23325906, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19776117HCID 19776117, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

63.2 g of methyl 10-(4-heptylphenyl)-10-hydroxydecanoate are converted to the sodium alcoholate with 10 g of a 50% sodium hydride/liquid paraffin dispersion in 500 ml of dimethyl sulfoxide. When the evolution of hydrogen is complete, a solution of 69.6 g of 4-(4-mesyloxycyclohexyl)-butylcyclohexane (prepared from the corrsponding cyclohexanol with mesyl chloride/triethylamine in dichloromethane) in 120 ml of dimethyl sulfoxide is added dropwise at 20° C. Stirring is continued for a further 2 hours at 50° C., and the mixture is poured onto 2 liters of ice water and extracted with dichloromethane. The residue obtained after removal of the solvent is chromatographed over silica gel, using chloroform as the eluant. Methyl 10-(4-(4-butylcyclohexyl)-cyclohexyloxy)-10-(4-heptylphenyl)-decanoate is isolated.

Workup

  1. additionis added dropwise at 20° C
  2. extractionextracted with dichloromethane
  3. customThe residue obtained
  4. customafter removal of the solvent
  5. customis chromatographed over silica gel

Sources & evidence

ORD record
ord-9af42ff3b1604fd88617338e6dd2da8d
Source dataset
uspto-grants-1993_03
Patent number
US05190689

Reaction notes

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