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

Reaction equation

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

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 198716652-Methoxy-3,4-dimethyl-2-cyclopenten-1-one

Product 1

HCID 895392-Hydroxy-3,4-dimethyl-2-cyclopenten-1-oneYield 71.4%

Procedure

0.70 g (5 mmol) of crude 2-methoxy-3,4-dimethyl-2-cyclopenten-1-one is held at reflux temperature for 3 hours with 7 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 to give 0.45 g (71.4%) of 2-hydroxy-3,4-dimethyl-2-cyclopenten-1-one, content 90.6%. The data for this material are:

Workup

extractionThe reaction mixture is extracted 3 times with 50 ml of CH2Cl2 each time
dry with materialThe combined organic phases are dried over magnesium sulphate
concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record: ord-6d05db3d9a4c4f8da3858e4d157754a1
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04892966

Reaction notes

Loading…