Phenolate Sodium → HCID 53693383, compound

HRID 1981301Notes

Reaction equation

HRID 1981301 reaction equation
[C:1]1([O-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[Cl:9][C:10](Cl)=[CH:11][C:12]([CH3:16])([CH3:15])[CH:13]=[CH2:14]>CN(C)C=O.C(Cl)Cl>[Cl:9][CH:10]=[C:11]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:12]([CH3:16])([CH3:15])[CH:13]=[CH2:14]

Participants

5

Reactant 2

HCID 4445035Phenolate SodiumHCID 13089648HCID 13089648, compound

Product 1

HCID 53693383HCID 53693383, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

116 g (1 mol) of sodium phenolate and 82.5 g (0.5 mole) of 1,1-dichloro-3,3-dimethyl-1,4-pentadiene in 500 ml of dimethylformamide were heated under reflux for 8 hours. The solution was diluted with methylene chloride and extracted by shaking with dilute sodium hydroxide solution. After the methylene chloride phase had been dried over sodium sulphate, the solvent was stripped off in vacuo. The residual crude product was distilled in vacuo. 93.6 g (84% of theory) of 1-chloro-3,3-dimethyl-2-phenoxy-1,4-pentadiene of boiling point 80° to 90° C./0.5 mm Hg were obtained. ##STR26##

Workup

  1. temperatureunder reflux for 8 hours
  2. extractionextracted
  3. dry with materialAfter the methylene chloride phase had been dried over sodium sulphate
  4. distillationThe residual crude product was distilled in vacuo

Sources & evidence

ORD record
ord-b54c7deb18994b79bb8ab06a3772ee87
Source dataset
uspto-grants-1985_04
Patent number
US04514409

Reaction notes

Loading…