Hydrochloric Acid → 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one

HRID 329811Notes

Reaction equation

HRID 329811 reaction equation
C[O:2][C:3]1[C:4](=[O:11])[CH:5]([CH3:10])[CH:6]([CH3:9])[C:7]=1[CH3:8].Cl>>[OH:11][C:4]1[C:3](=[O:2])[CH:7]([CH3:8])[CH:6]([CH3:9])[C:5]=1[CH3:10]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 198716692-Methoxy-3,4,5-trimethyl-2-cyclopenten-1-one

Product 1

HCID 5287072-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-oneYield 72.9%

Procedure

5.39 g (35 mmol) of 2-methoxy-3,4,5-trimethyl-2-cyclopenten-1-one are held at reflux temperature for 90 minutes with 53.9 g (10 fold amount by weight) of 5N hydrochloric acid. The reaction mixture is extracted 3 times with 50 ml of ether each time. The combined organic phases are dried over magnesium sulphate and concentrated on a rotary evaporator. The crude product is distilled at 45°-48° C./0.03 mbar and yields 3.57 g (72.9%) of 2-hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one.

Workup

  1. extractionThe reaction mixture is extracted 3 times with 50 ml of ether each time
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. concentrationconcentrated on a rotary evaporator
  4. distillationThe crude product is distilled at 45°-48° C./0.03 mbar

Sources & evidence

ORD record
ord-e9e6388bfc2141a1b5c3bb80f3bbd920
Source dataset
uspto-grants-1990_01
Patent number
US04892966

Reaction notes

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