Dimethylformamide → Diisopropyl Ether

HRID 1702738Notes

Reaction equation

HRID 1702738 reaction equation
[C:1]1([CH:7]([C:11]([OH:13])=O)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O.CN(C)C=O.[CH:23]([OH:36])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OC(C)C)(C)C>[CH:1]([O:36][CH:23]([CH3:24])[CH3:30])([CH3:6])[CH3:2].[C:1]1([CH:7]([C:8]([O:10][CH:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:9])[C:11]([Cl:16])=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7037BenzhydrolHCID 24386Thionyl ChlorideHCID 75791Phenylmalonic acid2×

Product 2

HCID 7914Diisopropyl EtherHCID 20472690HCID 20472690, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

Following the procedure of Goldman et al. (U.S. Pat. No. 3,773,757), phenylmalonic acid (72 g., 0.40 mole), thionyl chloride (52.4 g., 0.44 mole) and dimethylformamide (0.070 ml.) are mixed in diisopropyl ether and refluxed for 2 hours. The resulting solution of phenylmalonic acid-half acid chloride is cooled and stored under an inert atmosphere until use. Following a procedure analogous to that of Goldman et al., benzhydryl alcohol (73.6 g., 0.40 mole) is added to the half-acid chloride solution and the mixture again refluxed for 2 hours. The volume is reduced by half, providing a diisopropylether solution of 2-phenyl-2-benzhydryloxycarbonylacetyl chloride used directly in the next step.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturethe mixture again refluxed for 2 hours

Sources & evidence

ORD record
ord-8492c9094a8b480ba4c844fbfdc97593
Source dataset
uspto-grants-1982_09
Patent number
US04348264

Reaction notes

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