Water → 2-Isopropyl 4-methylpent-4 enoic acid, alpha-cyano-3 phenoxybenzyl ester

HRID 441842Notes

Reaction equation

HRID 441842 reaction equation
[CH:1]([CH:4]([CH2:8][C:9]([CH3:11])=[CH2:10])[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2].[C:12]([CH:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1)#[N:13].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH:1]([CH:4]([CH2:8][C:9]([CH3:11])=[CH2:10])[C:5]([O:7][CH:14]([C:12]#[N:13])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:16]=1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12713810alpha-Cyano-3-phenoxybenzyl bromideHCID 149108594-Methyl-2-propan-2-ylpent-4-enoic acid

Product 1

HCID 1317108682-Isopropyl 4-methylpent-4 enoic acid, alpha-cyano-3 phenoxybenzyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-isopropyl-4-methylpent-4-enoic acid (1.0g), alpha-cyano-3-phenoxybenzyl bromide (1.9g) and potassium carbonate (1.0g) in anhydrous acetone (40ml) was stirred at room temperature for 4 hours. Water was added to the reaction mixture and the product extracted with ether, the ethereal extracts washed with water (X2) and dried over magnesium sulphate. Evaporation of the solvent gave a crude product which was purified by chromatography on silica gel using 3% acetone in 60°-80° C. petroleum ether as eluent to give the desired ester. R.I. nD20 1.5343.

Workup

  1. extractionthe product extracted with ether
  2. washthe ethereal extracts washed with water (X2)
  3. dry with materialdried over magnesium sulphate
  4. customEvaporation of the solvent
  5. customgave a crude product which
  6. customwas purified by chromatography on silica gel using 3% acetone in 60°-80° C. petroleum ether as eluent

Sources & evidence

ORD record
ord-36732275e3d3415d9b09f797ba180afb
Source dataset
uspto-grants-1977_08
Patent number
US04042710

Reaction notes

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