Sulfuric Acid → 4-Cyclohexyloxy-1-naphthol

HRID 904714

Reaction equation

HRID 904714 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([OH:12])=[CH:8][CH:9]=[C:10]([OH:11])[C:4]2=[CH:3][CH:2]=1.[CH:13]1(O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.S(=O)(=O)(O)O>C(OCC)(=O)C>[CH:13]1([O:12][C:7]2[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[C:10]([OH:11])=[CH:9][CH:8]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7966CyclohexanolHCID 113051,4-Naphthalenediol

Product 1

HCID 125635414-Cyclohexyloxy-1-naphtholYield 24.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

160 g of naphthohydroquinone and 416 g of cyclohexanol were placed in a 1 l three-necked flask, and 80 ml of concentrated sulfuric acid was dropwisely added thereto for 10 minutes under nitrogen gas stream while stirring. Thereafter, the reaction mixture was heated at 60° C. for 40 minutes and then cooled to room temperature. The reaction mixture was extracted with 500 ml of ethyl acetate. The ethyl acetate layer was washed with water until the washing reached neutral and, then, dried with MgSO4 overnight. The dried ethyl acetate solution was concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 140 g of oily substance. The oily substance was dissolved in ethyl acetate and treated with about 20 g of active carbon followed by concentration under reduced pressure. The residue was recrystallized from benzene two times to obtain 60 g of white crystals having a melting point of 120° to 121° C.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe reaction mixture was extracted with 500 ml of ethyl acetate
  3. washThe ethyl acetate layer was washed with water until the washing
  4. dry with materialdried with MgSO4 overnight
  5. concentrationThe dried ethyl acetate solution was concentrated under reduced pressure
  6. distillationThe residue was distilled under reduced pressure
  7. customto obtain 140 g of oily substance
  8. additiontreated with about 20 g of active carbon
  9. concentrationfollowed by concentration under reduced pressure
  10. customThe residue was recrystallized from benzene two times

Sources & evidence

ORD record
ord-1903fd7dc7ad4232aaebac8cf2a00aed
Source dataset
uspto-grants-1983_12
Patent number
US04419439

Linked notes

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