Sodium hydride → (trans) 3,3,5-Trimethylcyclohexyl 2-(4-phenylphenoxy)-2-methylpropionate

HRID 1033233Notes

Reaction equation

HRID 1033233 reaction equation
[C:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:23][C:24]1([CH3:32])[CH2:29][C@@H:28]([CH3:30])[CH2:27][C@H](O)[CH2:25]1>CCCCCCC>[C:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15][C@H:16]3[CH2:27][C@H:28]([CH3:30])[CH2:29][C:24]([CH3:32])([CH3:25])[CH2:23]3)=[O:14])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1550824Cyclohexanol, 3,3,5-trimethyl-, trans-HCID 19025875HCID 19025875, compound

Product 1

HCID 86747831(trans) 3,3,5-Trimethylcyclohexyl 2-(4-phenylphenoxy)-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

27 g of methyl 2-(4-phenylphenoxy)-2-methylpropionate (0.1 mol) and 0. 3 g of sodium hydride as a 60% dispersion in oil are added to 14.2 g of (trans) 3,3,5-trimethylcyclohexanol (0.1 mol) dissolved in 500 ml of heptane. The stirred mixture is brought to the boil in a distillation apparatus appropriately equipped for progressively separating the binary heptane/methanol mixture, which boils at 59° C.; the operation requires 4 to 5 hours; the mixture is cooled and then washed carefully with an alkaline aqueous solution, then an acidic aqueous solution and finally pure water. After chromatography on a silica column with a mixture of ethyl acetate and petroleum ether and recrystallization from 90% isopropanol, the title derivative is obtained in the form of silky crystals melting at 96° C. TLC performed under the previous conditions gives a single spot of Rf 0. 90. The IR spectrum has characteristic bands at 2950-2850, 1745 and 1640 cm-1.

Workup

  1. customappropriately equipped
  2. customfor progressively separating the binary heptane/methanol mixture, which boils at 59° C.
  3. temperaturethe mixture is cooled
  4. washwashed carefully with an alkaline aqueous solution
  5. additionAfter chromatography on a silica column with a mixture of ethyl acetate and petroleum ether and recrystallization from 90% isopropanol

Sources & evidence

ORD record
ord-2f34bca060aa4220b198fbad13737d97
Source dataset
uspto-grants-1994_05
Patent number
US05310757

Reaction notes

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