1-Hexanol → HCID 20552037, compound

HRID 851838Notes

Reaction equation

HRID 851838 reaction equation
[CH:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[CH2:12]([OH:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>C1(C)C=CC=CC=1.CCCCCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:12]([O:18][C:7]([CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]1[C:10]([O:9][CH2:5][CH2:6][CH2:1][CH2:2][CH2:3][CH3:4])=[O:11])=[O:8])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 2

HCID 81031-HexanolHCID 85689Hexahydrophthalic anhydride

Product 1

HCID 20552037HCID 20552037, compoundYield 120.7%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

A mixture of 1,2-cyclohexanedicarboxylic anhydride (60 g), hexanol (85 g), and p-toluenesulfonic acid (100 mg) in toluene (500 mL) was refluxed for 3 days and water removed from the reaction mixture. After reaction was complete, solvent was removed in vacuo to yield a viscous oil. The crude material was redissolved in heptane and passed through a pad of silica gel to obtain cyclohexane-1,2-dicarboxylic acid dihexyl ester (80 g) as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-a4e6d1139b8d43faa72d2c4e14579a28
Source dataset
uspto-grants-2007_08
Patent number
US07252865B2

Reaction notes

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