Hydrochloric Acid → 2-Oxobicyclo(3.1.0)hexane-6-carboxylic acid

HRID 582850

Reaction equation

HRID 582850 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]2[CH:3]1[CH:4]2[C:8]([O:10]CC)=[O:9].Cl>[OH-].[Na+]>[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]2[CH:3]1[CH:4]2[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 565357Ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate

Product 1

HCID 102194732-Oxobicyclo(3.1.0)hexane-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
27.5 °C

Procedure

A mixture of 60 g of ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate and 300 ml of 1N sodium hydroxide was stirred at 25-30° C. After 2.5 hours, concentrated hydrochloric acid was added to adjust the pH to 0.8-1.2. The resulting solution was extracted with ethyl acetate. The extracts were dried over magnesium sulfate, filtered, and concentrated to give 49.1 g (98%) of the crude material. Recrystallization from 100 ml of ethyl acetate gave the title compound, mp 123.5-128° C.

Workup

  1. extractionThe resulting solution was extracted with ethyl acetate
  2. dry with materialThe extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give 49.1 g (98%) of the crude material
  6. customRecrystallization from 100 ml of ethyl acetate

Sources & evidence

ORD record
ord-8eb0ecb922d641a1b4197c564caa7971
Source dataset
uspto-grants-1999_07
Patent number
US05925782

Linked notes

Loading…