Cyclohexanol → Cyclohexyl Hydrogen Phenylmalonate

HRID 36903

Reaction equation

HRID 36903 reaction equation
[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH:18]1(O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CCOCC.CN(C)C=O>[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([O:10][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 7966CyclohexanolHCID 24386Thionyl ChlorideHCID 75791Phenylmalonic acid

Product 1

HCID 19042990Cyclohexyl Hydrogen Phenylmalonate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Phenylmalonic acid (13.5 g, 0.07 mol) in dry ether (40 mL) was treated with thionyl chloride (8.92 g, 5.4 mL, 0.07 mol) and one drop of N,N-dimethylformamide. The mixture was heated at 40°-50° C. for 3 hours. The clear solution was distilled under vacuum. The oily residue was redissolved in dry ether (40 mL), the solution was treated with cyclohexyl alcohol (0.075 mol, 7.9 mL) and refluxed for 2 hours. The mixture was worked up as before to give an oily product which crystallized on standing. Recrystallization was carried out from a benzenepetroleum ether (40°-60°) mixture to give a white crystalline product.

Workup

  1. temperatureThe mixture was heated at 40°-50° C. for 3 hours
  2. distillationThe clear solution was distilled under vacuum
  3. dissolutionThe oily residue was redissolved in dry ether (40 mL)
  4. temperaturerefluxed for 2 hours
  5. customto give an oily product which
  6. customcrystallized
  7. customRecrystallization
  8. customwas carried out from a benzenepetroleum ether (40°-60°) mixture
  9. customto give a white crystalline product

Sources & evidence

ORD record
ord-ac0b0d8f6fdf49b792a5870d4b32ad56
Source dataset
uspto-grants-1995_05
Patent number
US05418244

Linked notes

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