Hydrochloric Acid → 4-(Cyclohexyloxy)phenol

HRID 237768Notes

Reaction equation

HRID 237768 reaction equation
[CH:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([S-])C.[Na+].O.Cl>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([O:7][C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4459711Sodium ethanethiolateHCID 9942491HCID 9942491, compound

Product 1

HCID 135877164-(Cyclohexyloxy)phenolYield 45.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-cyclohexyloxy-4-methoxy-benzene (2.06 g, 10 mmol), prepared in accordance with the procedure of He, et. al., J. Am. Chem. Soc., 2005, 127, 6966, in DMF (20 mL) was added sodium ethanethiolate (1.15 g, 11 mmol). The reaction mixture was stirred at reflux for two hours. The reaction mixture was then cooled to room temperature. Water (5 mL) was added after which the mixture was neutralized with hydrochloric acid (2N). Ethyl acetate (200 mL) was then added and the organic phase washed with water three times, brine twice, and dried (Na2SO4). Silica gel chromatography (EtOAc/heptane) provided 0.88 g of the title compound.

Workup

  1. temperatureat reflux for two hours
  2. washthe organic phase washed with water three times, brine twice
  3. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-97cddf34a52b4f4eb6250289866a53ab
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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