HCID 53693383, compound → HCID 13102421, compound

HRID 905354Notes

Reaction equation

HRID 905354 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 were warmed to 40° C. in a mixture of 250 ml of formic acid and 50 ml of concentrated hydrochloric acid for 1 hour. The mixture was then diluted with 400 ml of CH2Cl2 and ice, and was extracted 3 times by shaking with 2 N sodium hydroxide solution. After the methylene chloride phase had been dried over Na2SO4, the solvent was stripped off in a rotary evaporator. There remained 36 g (96%) of crude product. 32.2 g (0.22 mol, 86%) of 1-chloro-3,3-dimethyl-pent-4-en-2-one were obtained by distillation (b.p. 81°-84° C./24 mm Hg).

Workup

  1. extractionwas extracted 3 times
  2. dry with materialAfter the methylene chloride phase had been dried over Na2SO4
  3. customthe solvent was stripped off in a rotary evaporator

Sources & evidence

ORD record
ord-22e5ffa08b7a417e9a06bcd0bad187d4
Source dataset
uspto-grants-1983_12
Patent number
US04423243

Reaction notes

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