Cyclohexanol → HCID 58612895, compound

HRID 851839

Reaction equation

HRID 851839 reaction equation
[CH2:1]([C:10]([OH:12])=[O:11])[CH:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[CH:13]1(O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1.CCCCCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:13]1([O:5][C:4]([CH2:3][CH:2]([C:7]([O:9][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:8])[CH2:1][C:10]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:11])=[O:6])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 2

HCID 7966CyclohexanolHCID 149251,2,3-Propanetricarboxylic acid

Product 1

HCID 58612895HCID 58612895, compoundYield 83.4%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

A mixture of 1,2,3-propanetricarboxylic acid (25 g), cyclohexanol (55 g), and p-toluenesulfonic acid (100 mg) in toluene (500 mL) was refluxed for 2 days and water removed from the reaction mixture. After reaction was complete, solvent was removed in vacuuo to yield a viscous oil. The crude material was redissolved in heptane and passed through a pad of silica gel to obtain 1,2,3-propanetricarboxylic acid tricyclohexyl ester (50 g) as a pale yellow oil.

Workup

  1. temperaturewas refluxed for 2 days
  2. customwater removed from the reaction mixture
  3. customAfter reaction
  4. customsolvent was removed in vacuuo
  5. customto yield a viscous oil

Sources & evidence

ORD record
ord-7e233837b41f4ef9a3784255f4e715dd
Source dataset
uspto-grants-2007_08
Patent number
US07252865B2

Linked notes

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