Potassium Hydroxide → HCID 178525735, compound

HRID 1461993Notes

Reaction equation

HRID 1461993 reaction equation
[C@H:1]1([C:17]([O:19]CC2C=CC=CC=2)=[O:18])[CH2:6][CH2:5][C@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3][CH2:2]1.[OH-].[K+]>C(O)(C)(C)C>[CH2:10]([O:9][C:7]([C@H:4]1[CH2:5][CH2:6][C@H:1]([C:17]([OH:19])=[O:18])[CH2:2][CH2:3]1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178525076HCID 178525076, compound

Product 1

HCID 178525735HCID 178525735, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a solution of 1.0 g (2.8 mmole) dibenzyl trans-1,4-cyclohexanedicarboxylate in 20 ml tert.-butanol (warm) is added a solution of 1.9 g potassium hydroxide in 10 ml tert.-butanol. After stirring at room temperature overnight the cloudy mixture is evaporated to remove solvent, taken up in water and acidified to pH 5.3; then, after 30 minutes, acidified to pH 5.25 with dilute hydrochloric acid. The precipitated solid is collected on a filter, redissolved in dilute sodium bicarbonate solution and this readjusted to pH 5.25 to precipitate the purified monoester 1H-NMR (DMSO-D6) ppm (delta): 1.1-2.3 (m, 10H), 5.1 (s, 1H), 7.35 (s, 5H).

Workup

  1. customis evaporated
  2. customto remove solvent
  3. waitthen, after 30 minutes
  4. customThe precipitated solid is collected on a filter
  5. dissolutionredissolved in dilute sodium bicarbonate solution
  6. customto precipitate the purified monoester 1H-NMR (DMSO-D6) ppm (delta): 1.1-2.3 (m, 10H), 5.1 (s, 1H), 7.35 (s, 5H)

Sources & evidence

ORD record
ord-464234c127af474090b3b90522d370c0
Source dataset
uspto-grants-1984_07
Patent number
US04457924

Reaction notes

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