Phenolate Sodium → HCID 53993923, compound

HRID 2073410Notes

Reaction equation

HRID 2073410 reaction equation
Cl[C:2]([Cl:12])=[CH:3][C:4]([CH2:10][CH3:11])([CH3:9])[CH2:5][CH2:6][CH2:7][CH3:8].[C:13]1([O-:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Na+]>CN(C)C=O.C(Cl)Cl>[Cl:12][CH:2]=[C:3]([O:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]([CH2:10][CH3:11])([CH3:9])[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 4445035Phenolate SodiumHCID 13849834HCID 13849834, compound

Product 1

HCID 53993923HCID 53993923, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

626 g (3 moles) of 1,1-dichloro-3-ethyl-3-methyl-1-heptene and 676 g (6 moles) of sodium phenolate are heated under relfux in 3 l of dimethylformamide for 16 hours. The mixture is diluted with methylene chloride and extracted by shaking several times with 2N aqueous sodium hydroxide solution. After drying and evaporating on a rotary evaporator, 666 g of crude product remain. Distillation at boiling point0.1 100°-110° C. gives 523 g (65% of theory) of 1-chloro-3-ethyl-3-methyl-2-phenoxy-hept-1-ene.

Workup

  1. extractionextracted
  2. customAfter drying
  3. customevaporating on a rotary evaporator, 666 g of crude product
  4. distillationDistillation
  5. customat boiling point0.1 100°-110° C.

Sources & evidence

ORD record
ord-bd83b4e780b64b329099077e5f87a30f
Source dataset
uspto-grants-1990_04
Patent number
US04917720

Reaction notes

Loading…