3,3,5-Trimethylcyclohexanol → HCID 86747827, compound

HRID 1033229Notes

Reaction equation

HRID 1033229 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH:6]([CH3:8])[CH2:5][CH:4]([OH:9])[CH2:3]1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:39]=[CH:38][C:22]([C:23]([C:25]2[CH:37]=[CH:36][C:28]([O:29][C:30]([CH3:35])([CH3:34])[C:31](Cl)=[O:32])=[CH:27][CH:26]=2)=[O:24])=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[Cl:18][C:19]1[CH:39]=[CH:38][C:22]([C:23]([C:25]2[CH:37]=[CH:36][C:28]([O:29][C:30]([CH3:35])([CH3:34])[C:31]([O:9][C@H:4]3[CH2:5][C@@H:6]([CH3:8])[CH2:7][C:2]([CH3:10])([CH3:1])[CH2:3]3)=[O:32])=[CH:27][CH:26]=2)=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 82983,3,5-TrimethylcyclohexanolHCID 8471TriethylamineHCID 190258652-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoyl chloride

Product 1

HCID 86747827HCID 86747827, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

5 g of 3,3,5-trimethylcyclohexanol, CIS form, and then 3.5 g of triethylamine dissolved in 10 ml of chloroform are added to 50 ml of pure chloroform. 12 g of 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionyl chloride diluted in a few ml of chloroform are then added slowly to the solution at low temperature. The mixture is refluxed for three hours and then, after cooling, the organic layer is washed successively with a normal solution of hydrochloric acid, sodium hydroxide and then distilled water. It is evaporated under reduced pressure and the residue is then chromatographed on a silica column with a mixture of petroleum ether and ethyl acetate and finally recrystallized from ethanol to give the title derivative in the form of attractive white crystals melting at 65° C., which in thin layer chromatography give a single spot of Rf 0.45 in the solvent system described in Example 1.

Workup

  1. additionare then added slowly to the solution at low temperature
  2. temperatureThe mixture is refluxed for three hours
  3. temperatureafter cooling
  4. washthe organic layer is washed successively with a normal solution of hydrochloric acid, sodium hydroxide
  5. customIt is evaporated under reduced pressure
  6. customthe residue is then chromatographed on a silica column with a mixture of petroleum ether and ethyl acetate
  7. customfinally recrystallized from ethanol

Sources & evidence

ORD record
ord-00af16dad162441f9157c1b05c0348f3
Source dataset
uspto-grants-1994_05
Patent number
US05310757

Reaction notes

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