Phenolate Sodium → HCID 53993923, compound

HRID 1638243Notes

Reaction equation

HRID 1638243 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 696 g (6 moles) of sodium phenolate are heated under reflux in 3 L of dimethylformamide for 16 hours. The mixture is diluted with methylene chloride and extracted by shaking several times with 2 N 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. NMR (CDCl3): δ 0.7-1.6 (m, 17 H), 5.8 and 5.85 (2 s, 1 H) and 6.8-7.4 (m, 5 H). ##STR60##

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-01196e04fbdb4aceb73dcd242f73d073
Source dataset
uspto-grants-1989_11
Patent number
US04878939

Reaction notes

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