Dimethylformamide → Diisopropyl Ether

HRID 2296579Notes

Reaction equation

HRID 2296579 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 l 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-027f4c368e4145b49a4dc7f4e9b353c6
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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