3,3-Bis(ethoxycarbonyl)bicyclo[3.2.0]heptane → Bicyclo[3.2.0]heptane-3,3-dicarboxylic acid

HRID 1764177Notes

Reaction equation

HRID 1764177 reaction equation
C([O:3][C:4]([C:6]1([C:13]([O:15]CC)=[O:14])[CH2:12][CH:11]2[CH:8]([CH2:9][CH2:10]2)[CH2:7]1)=[O:5])C.CO.O>[OH-].[K+]>[CH:8]12[CH2:9][CH2:10][CH:11]1[CH2:12][C:6]([C:13]([OH:15])=[O:14])([C:4]([OH:5])=[O:3])[CH2:7]2

Participants

4

Reactant 2

HCID 213254333,3-Bis(ethoxycarbonyl)bicyclo[3.2.0]heptaneHCID 22242641Methanol--water (1/1)

Product 1

HCID 21325436Bicyclo[3.2.0]heptane-3,3-dicarboxylic acidYield 87.4%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of 10.3 g of 3,3-bis(ethoxycarbonyl)bicyclo[3.2.0]heptane in 68 ml of 16% potassium hydroxide in 1:1 methanol-water was refluxed for 16 hr under argon. The solvents were removed in vacuo and the residue dissolved in a minimum amount of water. The solution was acidified with concentrated hydrochloric acid and the precipitated acid isolated by vacuum filtration to yield 6.9 g of bicyclo[3.2.0]heptane-3,3-dicarboxylic acid as a white solid, mp 161°-170°.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue dissolved in a minimum amount of water
  3. customthe precipitated acid isolated by vacuum filtration

Sources & evidence

ORD record
ord-d6ab689ada524527a5ecbd590a9c70aa
Source dataset
uspto-grants-1978_09
Patent number
US04115453

Reaction notes

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