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

HRID 329809Notes

Reaction equation

HRID 329809 reaction equation
C[O:2][C:3]1[C:4](=[O:10])[CH:5]([CH3:9])[CH2:6][C:7]=1[CH3:8].Cl>>[OH:10][C:4]1[C:3](=[O:2])[CH:7]([CH3:8])[CH2:6][C:5]=1[CH3:9]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 1121722-Cyclopenten-1-one, 2-methoxy-3,5-dimethyl-

Product 1

HCID 895382-Hydroxy-3,5-dimethyl-2-cyclopenten-1-oneYield 54.2%

Procedure

2.15 g (15.36 mmol) of crude 2-methoxy-3,5-dimethyl-2-cyclopenten-1-one are held at reflux temperature for 2 hours with 21.50 g (=10 fold amount by weight) of 5N hydrochloric acid. The reaction mixture is extracted 3 times with 50 ml of CH2Cl2 each time. The combined organic phases are dried over magnesium sulphate and concentrated on a rotary evaporator. After recrystallization from ether/hexane 1:1 there are obtained 1.05 g (54.2%) 2-hydroxy-3,5-dimethyl-2-cyclopenten-1-one; m.p. 92°-93° C.

Workup

  1. extractionThe reaction mixture is extracted 3 times with 50 ml of CH2Cl2 each time
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. concentrationconcentrated on a rotary evaporator
  4. customAfter recrystallization from ether/hexane 1:1 there

Sources & evidence

ORD record
ord-63a0285508a44711b0ed50e52b2a6e79
Source dataset
uspto-grants-1990_01
Patent number
US04892966

Reaction notes

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