HCID 53693383, compound → HCID 13102421, compound

HRID 1981302Notes

Reaction equation

HRID 1981302 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

Conditions

Temperature
40 °C

Procedure

57 g (0.256 mol) of 1-chloro-3,3-dimethyl-2-phenoxy-1,4-pentadiene in a mixture of 250 ml of formic acid and 50 ml of concentrated hydrochloric acid were heated to 40° C. in the course of 1 hour. The mixture was then diluted with 400 ml of methylene chloride and ice, and was extracted three times by shaking with 2N sodium hydroxide solution. After the methylene chloride phase had been dried over sodium sulphate, the solvent was removed. 36 g of product (96% of theory) remained and were distilled. 32.2 g (86% of theory) of 5-chloro-3,3-dimethylpent-1-en-4-one of boiling point 81° to 84° C./24 mm Hg were obtained. ##STR27##

Workup

  1. extractionwas extracted three times
  2. dry with materialAfter the methylene chloride phase had been dried over sodium sulphate
  3. customthe solvent was removed
  4. distillationwere distilled

Sources & evidence

ORD record
ord-8de7d33b49b7445b9c3eff2269f19787
Source dataset
uspto-grants-1985_04
Patent number
US04514409

Reaction notes

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