Hydrochloric Acid → 5-Cyclopentylidene-2-methylpentan-2-ol

HRID 2185166Notes

Reaction equation

HRID 2185166 reaction equation
[C:1]1(=[CH:6][CH2:7][CH2:8][C:9](=[O:11])[CH3:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:12][Mg]Br.Cl>CCOCC>[C:1]1(=[CH:6][CH2:7][CH2:8][C:9]([CH3:12])([OH:11])[CH3:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 135280135-Cyclopentylidenepentan-2-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 184338645-Cyclopentylidene-2-methylpentan-2-olYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

5-Cyclopentylidene-2-pentanone (13.4 g; 88 mmol) in ether (13 ml) was added dropwise during 30 minutes to a 3M solution of methylmagnesium bromide in ether (38 ml; 114 mmol). After addition of more ether (25 ml), the mixture was heated under reflux for 2 hours, then cooled down to room temperature, poured into ice (40 g), acidified with 5N HCl (50 ml) and extracted with MTBE (130 ml). The aqueous phase was separated and extracted with MTBE (2×130 ml). The combined organic phases were washed with saturated NaHCO3 (2×130 ml), water (130 ml), dried over MgSO4 and concentrated in vacuo. Distillation (52° C.-55° C./0.06 torr) yielded 11.24 g (76% yield) of 5-cyclopentylidene-2-methylpentan-2-ol.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with MTBE (130 ml)
  4. customThe aqueous phase was separated
  5. extractionextracted with MTBE (2×130 ml)
  6. washThe combined organic phases were washed with saturated NaHCO3 (2×130 ml), water (130 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. distillationDistillation (52° C.-55° C./0.06 torr)

Sources & evidence

ORD record
ord-90e857df120340468ffc516172f0fe5e
Source dataset
uspto-grants-2002_06
Patent number
US06399811B1

Reaction notes

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