1-Decanol → HCID 10428617, compound

HRID 728688Notes

Reaction equation

HRID 728688 reaction equation
C1[O:6][C:5]([CH2:11][C:12]([OH:14])=[O:13])([CH2:7][C:8]([OH:10])=[O:9])[C:3](=[O:4])[O:2]1.C(N([CH2:20][CH3:21])CC)C.[CH2:22](O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(O)C>[CH2:22]([CH:7]([C:5]([CH2:11][C:12]([OH:14])=[O:13])([C:3]([OH:2])=[O:4])[OH:6])[C:8]([OH:10])=[O:9])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 81741-DecanolHCID 8471TriethylamineHCID 8945Anhydromethylenecitric acid

Product 1

HCID 10428617HCID 10428617, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2 (50 g), triethylamine (75 ml) and decanol (110 ml) in ethanol-free chloroform (500 ml) was refluxed for 42 hours. GC analysis indicated a 10:1 mixture of the 2- and 1-monodecyl ester in addition to about 9% of unreacted starting material. Processing as indicated above gave the crude product (69.6 g, 86%) as an opalescent oil. This oil was dissolved in hot toluene (200 ml) on the steam bath, filtered from a small amount of insoluble material, which was washed with two additional portions of hot toluene (50 ml) and the combined filtrates cooled at room temperature.

Workup

  1. temperaturewas refluxed for 42 hours
  2. additionin addition to about 9%

Sources & evidence

ORD record
ord-05937b04ac244721b230b23e3cbedc97
Source dataset
uspto-grants-1991_09
Patent number
US05049699

Reaction notes

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