Hydrochloric Acid → 3-Ethyl-2-hydroxy-2-cyclopenten-1-one

HRID 329814Notes

Reaction equation

HRID 329814 reaction equation
[CH2:1]([C:3]1[CH2:7][CH2:6][C:5](=[O:8])[C:4]=1[O:9]C)[CH3:2].Cl>>[CH2:1]([C:3]1[CH2:7][CH2:6][C:5](=[O:8])[C:4]=1[OH:9])[CH3:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 115573013-Ethyl-2-methoxy-2-cyclopenten-1-one

Product 1

HCID 627523-Ethyl-2-hydroxy-2-cyclopenten-1-oneYield 65.7%

Procedure

3.08 g (22 mmol) of 3-ethyl-2-methoxy-2-cyclopenten-1-one are held at reflux temperature for 5 hours with 30.80 g of 5N hydrochloric acid. After cooling 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. The crude product is bulb-tube distilled at 0.1 mbar/110° C. and gives 1.82 g (65.7%) of 3-ethyl-2-hydroxy-2-cyclopenten-1-one (melting point 39°-41° C.).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionis extracted 3 times with 50 ml of CH2Cl2 each time
  3. dry with materialThe combined organic phases are dried over magnesium sulphate
  4. concentrationconcentrated on a rotary evaporator
  5. distillationdistilled at 0.1 mbar/110° C.

Sources & evidence

ORD record
ord-a44d580fb8e14c2491e294f1e2ee7aab
Source dataset
uspto-grants-1990_01
Patent number
US04892966

Reaction notes

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