Hexahydrophthalic anhydride, cis- → Cyclohexanecarboxylic acid

HRID 1836075Notes

Reaction equation

HRID 1836075 reaction equation
[C@@H:1]12C(=O)[O:9][C:7](=[O:8])[C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2>O1CCCC1.CN(C)C1C=CN=CC=1>[CH:2]1([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:1]1

Participants

4

Reactant 1

HCID 641660Hexahydrophthalic anhydride, cis-

Product 1

HCID 7413Cyclohexanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In 90 ml tetrahydrofuran, 48.1 g of cis-1,2-cyclohexanedicarboxylic anhydride, 46.3 g of the (1,4,4-trimethyl-3,5-dioxyanyl)methane-1-ol prepared in Synthesis Example 1 and 1.8 g of 4-(dimethylamino)pyridine were dissolved, and the resulting mixture was refluxed for 6 hours under heating. After the elimination of the tetrahydrofuran by distillation, the mixture was subjected to silica gel column chromatography to yield 54.7 g of 2-((1,4,4-trimethyl-3,5-dioxanyl) methyl) oxycarbonyl) cyclohexanecarboxylic acid.

Workup

  1. dissolutionwere dissolved
  2. temperaturethe resulting mixture was refluxed for 6 hours
  3. temperatureunder heating
  4. distillationAfter the elimination of the tetrahydrofuran by distillation

Sources & evidence

ORD record
ord-1fde7a904ab3486ba96ab36c64121210
Source dataset
uspto-grants-2004_08
Patent number
US06777155B2

Reaction notes

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