Sulfuric Acid → HCID 13717262, compound

HRID 1413087Notes

Reaction equation

HRID 1413087 reaction equation
[CH3:1][Mg]I.[CH:4]([C:7]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])([CH3:6])[CH3:5].S(=O)(=O)(O)O>CCOCC>[C:13]([C:7]1([CH:4]([CH3:6])[CH3:5])[CH2:11][CH2:10][CH2:9][C:8]1([CH3:1])[OH:12])([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11117016HCID 11117016, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 13717262HCID 13717262, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Methylmagnesium iodide (0.22 mole) in ether (200 ml.) was added dropwise to a solution of 2-isopropyl-2-carbethoxycyclopentanone (40 g, 0.2 mole) in ether (150 ml.), and the mixture was heated under reflux for 17 hours. Dilute sulphuric acid was then added and the ether layer was separated and dried (MgSO4). The ether was removed to leave 2-carbethoxy-1-methyl-2-isopropylcyclopentanol. This compound was dissolved in pyridine (200 ml.) and cooled to -10° C. Thionyl chloride (25 ml.) was then added keeping the temperature at -5° C. After 2 hours at -5° C., ether (500 ml) and an excess of 2 N sulphuric acid were added and the organic layer was separated. The aqueous layer was extracted with ether and the combined extracts were dried (MgSO4). The solvent was removed and the residue was distilled to give 1-carbethoxy-1-isopropyl-2-methylcyclopent-2-ene, bp. 107°-110°/17 mm.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 17 hours
  3. customthe ether layer was separated
  4. dry with materialdried (MgSO4)
  5. customThe ether was removed

Sources & evidence

ORD record
ord-3e82181c7c094faa84c7fe6694a5b97e
Source dataset
uspto-grants-1981_02
Patent number
US04248859

Reaction notes

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