Sodium Hydroxide → trans-1,2-Dimethylcyclohexene-4,5-dicarboxylic acid

HRID 128771Notes

Reaction equation

HRID 128771 reaction equation
[CH3:1][C:2]1[CH2:7][C@@H:6]([C:8]([O:10]C)=[O:9])[C@H:5]([C:12]([O:14]C)=[O:13])[CH2:4][C:3]=1[CH3:16].[OH-].[Na+]>CO>[CH3:16][C:3]1[CH2:4][C@@H:5]([C:12]([OH:14])=[O:13])[C@H:6]([C:8]([OH:10])=[O:9])[CH2:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2767837dimethyl (1R,2R)-4,5-dimethyl-4-cyclohexene-1,2-dicarboxylate

Product 1

HCID 738867trans-1,2-Dimethylcyclohexene-4,5-dicarboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trans-dimethyl 1,2-dimethylcyclohex-1-ene-4,5-dicarboxylate (4.52 g, 0.02 mol) was refluxed with NaOH (4.0 g, 0.1 mol) in methanol (40 ml) for 4 hr. The solution was allowed to cool and partitioned between aqueous NaOH (2M, 50 ml) and ether (60 ml). The aqueous layer was then acidified (1M HCl) and extracted with ethyl acetate (3×50 ml). The solvent was removed in vacuo to give the title compound in 77% yield. N.m.r: δH (90 MHz CD3Cl3) 2.58 (m,2H), 2.08 (m,4H), 1.70 ppm (s,6H)

Workup

  1. temperatureto cool
  2. custompartitioned between aqueous NaOH (2M, 50 ml) and ether (60 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b24dee3d3af440fba6afe77760606194
Source dataset
uspto-grants-1995_11
Patent number
US05464873

Reaction notes

Loading…