HCID 86679336, compound → HCID 61481477, compound

HRID 1464910Notes

Reaction equation

HRID 1464910 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][CH2:4][C:5]1(C(OC)=O)[CH2:9][CH2:8][CH2:7][C:6]1=[O:10]>C(O)(=O)C.Cl>[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][CH2:4][CH:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10]

Participants

4

Reactant 1

HCID 86679336HCID 86679336, compound

Product 1

HCID 61481477HCID 61481477, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution consisting of 23.0 g (101.7 mmol) of methyl 1-(3,3-dimethylbutyl)-2-oxocyclopentanecarboxylate in 80 ml of acetic acid and 80 ml of conc. hydrochloric acid is stirred at 90° C. for 14 hours. After the reaction has ended, the mixture is cooled to room temperature and ice-water is added. The product is extracted with diethyl ether. The org. phase is washed with water, dried with sodium sulphate and concentrated under reduced pressure. The crude product is purified by column chromatography (silica gel 60-120, mobile phase: ethyl acetate 3%/petroleum ether). This gives 10 g (59% of theory) of 2-(3,3-dimethylbutyl)cyclopentanone.

Workup

  1. temperaturethe mixture is cooled to room temperature
  2. extractionThe product is extracted with diethyl ether
  3. washphase is washed with water
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by column chromatography (silica gel 60-120, mobile phase: ethyl acetate 3%/petroleum ether)

Sources & evidence

ORD record
ord-b543c7164bae4a20979dbe2fa0afbf87
Source dataset
uspto-grants-2015_04
Patent number
US08999956B2

Reaction notes

Loading…