rel-(1S,5S)-3,3,5-Trimethylcyclohexanol → HCID 86747830, compound

HRID 1033232Notes

Reaction equation

HRID 1033232 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([CH3:13])([CH3:12])[C:9](Cl)=[O:10].[CH3:19][C:20]1([CH3:28])[CH2:25][C@H:24]([CH3:26])[CH2:23][C@H:22]([OH:27])[CH2:21]1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([CH3:13])([CH3:12])[C:9]([O:27][C@H:22]1[CH2:23][C@@H:24]([CH3:26])[CH2:25][C:20]([CH3:28])([CH3:19])[CH2:21]1)=[O:10]

Participants

4

Reactant 2

HCID 101921rel-(1S,5S)-3,3,5-TrimethylcyclohexanolHCID 144076195-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoyl chloride

Product 1

HCID 86747830HCID 86747830, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

25 g of 2-(3-(2,5-dimethylphenoxy)propyl)-2-methylpropionyl chloride are added to 14 g of (cis) 3,3,5-trimethylcyclohexanol dissolved in 100 ml of toluene. The mixture is refluxed for three hours and then evaporated to dryness. The evaporation residue is chromatographed on a silica column with chloroform. The title product is obtained in the amorphous state and in thin layer chromatography gives a single spot under the above conditions; the characteristic bands of its IR spectrum run in KBr are as follows: 3000-2850 cm-1, group of fine bands; 1730 cm-1, strong band for the carbonyl.

Workup

  1. temperatureThe mixture is refluxed for three hours
  2. customevaporated to dryness
  3. customThe evaporation residue is chromatographed on a silica column with chloroform

Sources & evidence

ORD record
ord-50f876555f6e409e926fa9dede7b91d9
Source dataset
uspto-grants-1994_05
Patent number
US05310757

Reaction notes

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