Isopropanol → Isopropyl Hydrogen Phenylmalonate

HRID 1588792Notes

Reaction equation

HRID 1588792 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](O)([CH3:20])[CH3:19]>CCOCC.CN(C)C=O>[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([O:10][CH:18]([CH3:20])[CH3:19])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 75791Phenylmalonic acid

Product 1

HCID 19042994Isopropyl Hydrogen PhenylmalonateYield 60%

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 evaporated under reduced pressure to remove any residual thionyl chloride. The oily residue was redissolved in dry ether (40 mL), and the solution was treated with isopropyl alcohol (0.075 mol, 5.76 mL), refluxed for 2 hours and worked up as before to give the titled compound

Workup

  1. temperatureThe mixture was heated at 40°-50° C. for 3 hours
  2. customThe clear solution was evaporated under reduced pressure
  3. customto remove any residual thionyl chloride
  4. dissolutionThe oily residue was redissolved in dry ether (40 mL)
  5. temperaturerefluxed for 2 hours

Sources & evidence

ORD record
ord-3ae712d35a354eb888a89e02653e9278
Source dataset
uspto-grants-1993_06
Patent number
US05223528

Reaction notes

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