Hydrochloric Acid → HCID 53644512, compound

HRID 615838Notes

Reaction equation

HRID 615838 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([CH:9]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]1)[CH:6]=[CH:7][CH3:8].Cl>C1C=CC=CC=1.N1C=CC=CC=1>[C:1]([O:14][CH:11]1[CH2:12][CH2:13][CH:9]([CH2:5][CH:6]=[CH:7][CH3:8])[CH2:10]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 54537312HCID 54537312, compound

Product 1

HCID 53644512HCID 53644512, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 2 ml of acetyl chloride in 5 ml of benzene was added at 0° C. to a solution of 1 g of 3-(2-butenyl)-cyclopentanol in 20 ml of benzene and 2 ml of pyridine and the mixture was stirred at 20° C. for 17 hours and was poured into 2N hydrochloric acid solution with stirring. The decanted aqueous phase was extracted with benzene and the organic phase was washed with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with a 9-1 cyclohexane-ethyl acetate mixture to obtain 1.4 g of 1-acetyloxy-3-(2-butenyl)-cyclopentane.

Workup

  1. stirringwith stirring
  2. extractionThe decanted aqueous phase was extracted with benzene
  3. washthe organic phase was washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with a 9-1 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-5405e9539eee490899787b1fef5af2d1
Source dataset
uspto-grants-1985_02
Patent number
US04501687

Reaction notes

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