Hydroxyphenylacetic acid → HCID 23369908, compound

HRID 1761963Notes

Reaction equation

HRID 1761963 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([OH:10])[CH2:3]1.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](O)=[O:21])=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:10][CH:4]2[CH2:3][C:2]([CH3:11])([CH3:1])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5]2)=[O:21])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 758513,3,5,5-Tetramethylcyclohexanol

Product 1

HCID 23369908HCID 23369908, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,3,5,5-Tetramethylcyclohexanol (7.81 g, 0.05 mol), 4-hydroxyphenylacetic acid (7.6 g, 0.05 mol), p-toluenesulfonic acid (2 g) and benzene (200 mL) were refluxed with continuous water separation for 8 hours. The reaction mixture was evaporated, the oily residue was dissolved in ethyl acetate (100 mL), washed first with aqueous 5% NaHCO3 solution (100 mL) and then twice with water (200 mL), then dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure to give 3,3,5,5-tetramethylcyclohexyl 4-hydroxyphenylacetate as a solid (7.00 g, 82.0% yield).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe oily residue was dissolved in ethyl acetate (100 mL)
  3. washwashed first with aqueous 5% NaHCO3 solution (100 mL)
  4. dry with materialtwice with water (200 mL), then dried over anhydrous MgSO4
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7b4136371f9c427584d139ef5cda1942
Source dataset
uspto-grants-1989_05
Patent number
US04829086

Reaction notes

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