Diethyl Ether → HCID 18980985, compound

HRID 482604Notes

Reaction equation

HRID 482604 reaction equation
[CH2:1]([O:4][CH:5]([CH3:8])[C:6]#N)[CH2:2][CH3:3].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1.C([O:20]CC)C>>[CH2:1]([O:4][CH:5]([CH3:8])[C:6]([C:13]1[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=1)=[O:20])[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 18980946HCID 18980946, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 18980985HCID 18980985, compound

Procedure

To 25 g (222 mmole) of 2-propoxypropionitrile (Example 96b) in 100 ml of diethyl ether was dropwise added 200 ml (200 mmole) of 1.0M 4-chlorophenylmagnesium bromide. After refluxing for 30 minutes the reaction mixture was cautiously quenched with 20 ml of water followed by a mixture of 25 ml of sulfuric acid and 75 ml of water. After stirring for 30 minutes the organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and distilled yielding 25.9 g of the title compound, bp 110°-125° C. at 0.3 torr.

Workup

  1. temperatureAfter refluxing for 30 minutes the reaction mixture
  2. customwas cautiously quenched with 20 ml of water
  3. additionfollowed by a mixture of 25 ml of sulfuric acid and 75 ml of water
  4. customwas separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. distillationdistilled

Sources & evidence

ORD record
ord-78243016b4f0428b9ca05b4ea2ead71e
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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