Hydroxyphenylacetic acid → 2,6-Dimethylcyclohexyl 4-hydroxyphenylacetate

HRID 846059

Reaction equation

HRID 846059 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[CH:3]1[OH:9].[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](O)=[O:19])=[CH:13][CH:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:9][CH:3]2[CH:4]([CH3:8])[CH2:5][CH2:6][CH2:7][CH:2]2[CH3:1])=[O:19])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 214282,6-Dimethylcyclohexanol

Product 1

HCID 541091042,6-Dimethylcyclohexyl 4-hydroxyphenylacetateYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,6-dimethylcyclohexyl alcohol (11.4 g), 4-hydroxyphenylacetic acid (9.12 g), p-toluenesulfonic acid (1 g) and benzene (300 mL) was refluxed with continuous water separation for 20 hours. The mixture was filtered and the filtrate was washed with a 10% Na2CO3 solution, then with water. Drying over MgSO4 and evaporation in vacuo afforded 8.02 g of 2,6-dimethylcyclohexyl 4-hydroxyphenylacetate. That product has the structural formula: ##STR25##

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed with a 10% Na2CO3 solution
  3. dry with materialDrying over MgSO4 and evaporation in vacuo

Sources & evidence

ORD record
ord-86f9c92bf1374738bd76e2681b2a2976
Source dataset
uspto-grants-1992_08
Patent number
US05135926

Linked notes

Loading…