Methanol → 1-Cyclohexene-1,2-dicarboxylic acid, dimethyl ester

HRID 128768Notes

Reaction equation

HRID 128768 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[N+](=[CH2:14])=[N-].[CH3:15][OH:16]>C(OCC)C>[CH3:15][O:16][C:4]([C:3]1[CH2:7][CH2:8][CH2:9][CH2:10][C:2]=1[C:1]([O:6][CH3:14])=[O:11])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 9550DiazomethaneHCID 124753,4,5,6-Tetrahydrophthalic anhydride

Product 1

HCID 780391-Cyclohexene-1,2-dicarboxylic acid, dimethyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3,4,5,6-tetrahydrophthalic anhydride (3.04 g, 0.02 mol) was disolved in methanol (25 ml) and refluxed for 2 hours. The solution was then cooled to ice bath temperature and a solution of diazomethane in diethyl ether was added dropwise until a yellow colour persisted. The solution was then allowed to stand overnight, after which time the solvent was removed in vacuo to give the title compound In 93% yield. δH (90 MHz, CDCl3) 3.66 (s,6H), 2.20 (s,4H), 1.66 ppm (s,6H)

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe solution was then cooled to ice bath temperature
  3. customafter which time the solvent was removed in vacuo

Sources & evidence

ORD record
ord-58fae3cc7a1d4f7eb415ad88c8607de5
Source dataset
uspto-grants-1995_11
Patent number
US05464873

Reaction notes

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