HCID 53693383, compound → HCID 13102421, compound

HRID 1462651Notes

Reaction equation

HRID 1462651 reaction equation
[Cl:1][CH:2]=[C:3]([O:9]C1C=CC=CC=1)[C:4]([CH3:8])([CH3:7])[CH:5]=[CH2:6]>C(O)=O.Cl.C(Cl)Cl>[Cl:1][CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH:5]=[CH2:6]

Participants

5

Reactant 1

HCID 53693383HCID 53693383, compound

Product 1

HCID 13102421HCID 13102421, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

57 g (0.256 mol) of 1-chloro-3,3-dimethyl-2-phenoxy-1,4-pentadiene (see Example A1(a)) are warmed to 40° C. in a mixture of 250 ml of formic acid and 50 ml of concentrated hydrochloric acid, during the course of 1 hour. The mixture is then diluted with 400 ml of methylene chloride and ice, and is three times extracted by shaking with 2N sodium hydroxide solution. After drying the methylene chloride phase over sodium sulphate, the solvent is removed. 36 g of product (96% of theory) remain, and this product is distilled. 32.2 g (86% of theory) of 1-chloro-3,3-dimethyl-pent-4-en-2-one are obtained at a boiling point of 81°-84° C./24 mm Hg.

Workup

  1. extractionextracted
  2. dry with materialAfter drying the methylene chloride phase over sodium sulphate
  3. customthe solvent is removed
  4. distillationthis product is distilled

Sources & evidence

ORD record
ord-ce8c7a4db42f4e679b9f1ed1a667ad16
Source dataset
uspto-grants-1984_07
Patent number
US04460793

Reaction notes

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