Hydroxyphenylacetic acid → HCID 23369908, compound

HRID 1761958Notes

Reaction equation

HRID 1761958 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12][C:13]1([CH3:22])[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][CH:15](O)[CH2:14]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH:15]2[CH2:16][C:17]([CH3:20])([CH3:19])[CH2:18][C:13]([CH3:22])([CH3:12])[CH2:14]2)=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

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

Product 1

HCID 23369908HCID 23369908, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-hydroxyphenylacetic acid (6.08 g), 3,3,5,5-tetramethylcyclohexyl alcohol (6.24 g), p-toluenesulfonic acid (1 g) and benzene (300 mL) was refluxed for 8 hours with continuous water separation. The mixture was cooled and washed with 10% Na2CO3, then with water. Drying over MgSO4 and evaporation in vacuo yielded 12.3 g of 3,3,5,5-tetramethylcyclohexyl 4-hydroxyphenylacetate. That product, which can be represented by the structural formula ##STR26## is characterized by the following NMR (CDCl3, TMS, ppm): 7.00(d, J=8 Hz, 2H), 6.60(d, J=8 Hz, 2H), 5.00(broad, 1H), 3.40(s, 2H) and 1.8-0.80(m, 18H).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with 10% Na2CO3
  3. dry with materialDrying over MgSO4 and evaporation in vacuo

Sources & evidence

ORD record
ord-35089a340b6a4f17a735ba89c015a00b
Source dataset
uspto-grants-1989_05
Patent number
US04829086

Reaction notes

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