Phenol → HCID 14297375, compound

HRID 2294898Notes

Reaction equation

HRID 2294898 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[C:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1.OS(O)(=O)=O>O>[CH2:18]([O:17][C:15]([CH:12]1[CH2:13][CH2:14][C:9]([C:4]2[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=2)([C:4]2[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=2)[CH2:10][CH2:11]1)=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 996PhenolHCID 1118Sulfuric AcidHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 14297375HCID 14297375, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Phenol (1.1 g, 11.8 mmol) was diluted with water (0.53 mL) and cooled to 0° C. with stirring. Ethyl 4-oxocyclohexanecarboxylate (0.94 mL, 5.87 mmol) was added followed by dropwise addition of concentrated H2SO4 (2.11 g). After 10 min the mixture was warmed to room temperature and allowed to stir for 4 hr. The mixture was then diluted with water and the product extracted with EtOAc (2×). The organic layer was washed with water, brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography (silica gel, 2:1 Hexane/EtOAc) to give 1.01 g (51%) of 4,4-bis(4-hydroxyphenyl)cyclohexane carboxylic acid ethyl ester.

Workup

  1. temperatureAfter 10 min the mixture was warmed to room temperature
  2. stirringto stir for 4 hr
  3. extractionthe product extracted with EtOAc (2×)
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (silica gel, 2:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-b210f78bbd12439a8a22b4fe27b3941e
Source dataset
uspto-grants-1997_11
Patent number
US05691351

Reaction notes

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