Methanol → (1R,2S)-2-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

HRID 2255221Notes

Reaction equation

HRID 2255221 reaction equation
[C@@H:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[CH3:12][OH:13]>>[CH3:12][O:13][C:7]([C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:1]1[C:10]([OH:9])=[O:11])=[O:8]

Participants

3

Reactant 2

HCID 887MethanolHCID 641660Hexahydrophthalic anhydride, cis-

Product 1

HCID 11008624(1R,2S)-2-(Methoxycarbonyl)cyclohexane-1-carboxylic acidYield 100%

Procedure

A mixture of 2 g (0.013 mol) of cis-1,2-cyclohexane-dicarboxylic anhydride in 15 mL of methanol was refluxed for 5 hr, then evaporated to dryness under reduced pressure to give 2.41 g (100% yield) of cis-2-methoxycarbonyl-cyclohexanecarboxylic acid. When this was substituted for 3 in Example 1, the identical process afforded the title compound, melting at 140°-144° C., in 36% yield; Rf (D)=0.53, 0.47.

Workup

  1. temperaturewas refluxed for 5 hr
  2. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f0821574381d42c2a2f416fb17225651
Source dataset
uspto-grants-1993_08
Patent number
US05239078

Reaction notes

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