Phenolate Sodium → HCID 131715636, compound

HRID 1761473Notes

Reaction equation

HRID 1761473 reaction equation
Cl[CH:2]=[CH:3][C:4]([CH3:9])([CH3:8])[C:5]#[C:6][Cl:7].[C:10]1([O-:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Na+]>CN(C)C=O>[Cl:7][CH:6]=[C:5]([O:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([CH3:9])([CH3:8])[C:3]#[CH:2]

Participants

4

Reactant 2

HCID 4445035Phenolate SodiumHCID 131715637HCID 131715637, compound

Product 1

HCID 131715636HCID 131715636, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

163 g (1 mole) of 1,5-dichloro-3,3-dimethyl-pent-1-en-4-ine and 232 g (2 moles) of sodium phenolate in 1 liter of absolute N,N-dimethylformamide are heated to 140° C. in the course of 3 hours and stirring is then continued for 4 hours. The mixture is worked up as described for method A, givign 204 g of crude product, which after distillation (boiling point 0.15/87°-94° C.) gives 141 g (that is to say 64% of theory) of 1-chloro-3,3-dimethyl-2-phenoxy-pent-1-en-4-ine.

Workup

  1. distillationafter distillation (boiling point 0.15/87°-94° C.)

Sources & evidence

ORD record
ord-7a64e838b3654a7fb1631357e1c811d4
Source dataset
uspto-grants-1989_05
Patent number
US04826865

Reaction notes

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