Cyclohexanol → HCID 17789168, compound

HRID 747671Notes

Reaction equation

HRID 747671 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:13]1(O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[CH:13]1([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 7966CyclohexanolHCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 17789168HCID 17789168, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

822 mg (4.95 mmol) of ethyl 4-hydroxybenzoate was dissolved in 20 ml of tetrahydrofuran. 545 mg (5.45 mmol) of cyclohexanol, 1.56 g (5.94 mmol) of triphenylphosphine and 202 mg (1.50 mmol) of diethyl azodicarboxylate were added to the solution, and they were stirred for 22 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was washed with 1 N sodium hydroxide and then with saturated aqueous NaCl solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe reaction liquid
  2. extractionAfter the extraction with ethyl acetate
  3. washthe organic layer was washed with 1 N sodium hydroxide
  4. dry with materialwith saturated aqueous NaCl solution, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-cc5753135cce445db60b3db6a2b6f447
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

Loading…