Hydrochloric Acid → 2-((3,3,5-Trimethylcyclohexyl)acetyl)cyclopentan-1-one

HRID 1461958Notes

Reaction equation

HRID 1461958 reaction equation
O1CCN([C:7]2[CH2:11][CH2:10][CH2:9][CH:8]=2)CC1.C(N(CC)CC)C.[CH3:19][C:20]1([CH3:31])[CH2:25][CH:24]([CH3:26])[CH2:23][CH:22]([CH2:27][C:28](Cl)=[O:29])[CH2:21]1.Cl.[OH2:33]>C(Cl)(Cl)Cl>[CH3:19][C:20]1([CH3:31])[CH2:25][CH:24]([CH3:26])[CH2:23][CH:22]([CH2:27][C:28]([CH:7]2[CH2:8][CH2:9][CH2:10][C:11]2=[O:33])=[O:29])[CH2:21]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 702941-MorpholinocyclopenteneHCID 20454255HCID 20454255, compound

Product 1

HCID 30200122-((3,3,5-Trimethylcyclohexyl)acetyl)cyclopentan-1-oneYield 58%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

111 g of freshly distilled morpholinocyclopentene, 71.7 g of triethylamine and 900 ml of chloroform are added to a round flask which is fitted with a thermometer, stirrer, reflux condenser and dropping funnel and the mixture is cooled to 0° C. Under a nitrogen atmosphere there are slowly added dropwise thereto 128 g of crude 3,3,5-trimethyl-cyclohexylacetyl chloride in 200 ml of chloroform. The flask content is stirred until it has reached a temperature of 20° C. and it is then warmed at 40° C. for a further 7 hours. After 12 hours, 76.2 of concentrated hydrochloric acid in 190 ml of water are added thereto and the flask content is held at reflux temperature for 21/2 hours. Thereafter, the organic phase is separated, the aqueous phase is extracted twice with chloroform and the combined chloroform extracts are washed as follows: three times with 10% hydrochloric acid, once with water, once with bicarbonate solution and finally with sodium chloride solution until neutral. Now it is concentrated in a rotary evaporator and the crude product (212 g) is distilled in vacuo. There are obtained 90 g (yield: 58%) of 2-(3,3,5-trimethylcyclohexylacetyl)-cyclopentanone.

Workup

  1. customis fitted with a thermometer, stirrer
  2. temperaturereflux condenser
  3. additionUnder a nitrogen atmosphere there are slowly added dropwise
  4. customa temperature of 20° C. and it
  5. temperatureis then warmed at 40° C. for a further 7 hours
  6. temperatureat reflux temperature for 21/2 hours
  7. customThereafter, the organic phase is separated
  8. extractionthe aqueous phase is extracted twice with chloroform
  9. washthe combined chloroform extracts are washed
  10. concentrationNow it is concentrated in a rotary evaporator
  11. distillationthe crude product (212 g) is distilled in vacuo

Sources & evidence

ORD record
ord-6659ec43a7ee41888731fff8ad51fe31
Source dataset
uspto-grants-1984_07
Patent number
US04457862

Reaction notes

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