p-Toluenesulfonic acid → Diheptyl galactarate

HRID 62569

Reaction equation

HRID 62569 reaction equation
[O:1]=[C:2]([OH:14])[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18](S(O)(=O)=O)=[CH:17][CH:16]=1>C[Re](=O)(=O)=O.C(O)CCCCCC>[O:1]=[C:2]([O:14][CH2:25][CH2:15][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([C:11]([O:13][CH2:25][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 3037582Galactaric acid

Product 1

HCID 131737197Diheptyl galactarate

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 8129HeptanolSolvent

Conditions

Temperature
150 °C

Procedure

In one specific embodiment of the present disclosure, 20 ml of 1-heptanol, 1 mmol of galactaric acid, 0.05 mmol of methyltrioxorhenium catalyst, and 0.05 mmol of para-toluenesulfonic acid were poured into a 50 cc reactor. The temperature in the reactor was then raised to 150° C. and the reaction was performed for 12 hours, maintaining the reactor temperature at 150° C. to obtain diheptyl galactarate.

Workup

  1. temperaturemaintaining the reactor temperature at 150° C.

Sources & evidence

ORD record
ord-f5e7bc175fbd42759b8032b4cebdc309
Source dataset
uspto-grants-2016_09
Patent number
US09447012B2

Linked notes

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