Cyclohexanol → Cyclohexyl Hydrogen Phenylmalonate

HRID 256577Notes

Reaction equation

HRID 256577 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 benzene-petroleum 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 benzene-petroleum ether (40-60°) mixture
  9. customto give a white crystalline product

Sources & evidence

ORD record
ord-a2ca22abcd1d419a844308e13789420f
Source dataset
uspto-grants-1993_11
Patent number
US05258388

Reaction notes

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