Stearic Acid → Octadecanoic acid, 26-hydroxy-3,6,9,12,15,18,21,24-octaoxahexacos-1-yl ester

HRID 1862181Notes

Reaction equation

HRID 1862181 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][OH:44])=[O:19].[C:45](O)(=[O:63])[CH2:46]CCCCCCCCCCCCCCCC>C1(C)C=CC=CC=1>[CH2:17]([C:18]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:46][CH2:45][OH:63])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

4

Reactant 2

HCID 5281Stearic AcidHCID 15557423-Hydroxy-3,6,9,12,15,18,21-heptaoxatricos-1-yl octadecanoate

Product 1

HCID 79303Octadecanoic acid, 26-hydroxy-3,6,9,12,15,18,21,24-octaoxahexacos-1-yl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

PEG400MS (polyethylene glycol 400 monostearate)—100 g (0.25 mol) of CARBOWAX™ 400 diol (commercially available from Union Carbide Corp., Danbury, Conn.) was combined with 71 g (0.25 mol) of stearic acid in 400 g of toluene in a 3-necked flask equipped with stirrer, heating mantle, thermometer and condenser. The contents were heated, azeotroped dry using a Dean Stark trap, and were allowed to cool. Next, 1.0 g (0 5% by weight of solids) of p-toluene sulfonic acid was added, and the mixture was refluxed with stirring overnight with the continuous removal of water. Infrared analysis indicated no acid carbonyl remained. A solution of 0.5 g of NaHCO3 in deionized water was then added. The resulting two-phase system was stirred and the water and toluene were removed at 80° C. using a ROTO-VAC™ evaporator to produce the desired monoester, C17H35C(O)O(C2H4O)8C2H4OH. This monostearate and its constituent reactants are presented as the first entry in TABLE 1.

Workup

  1. customequipped with stirrer
  2. temperatureheating mantle
  3. temperatureThe contents were heated
  4. customazeotroped
  5. customdry
  6. temperatureto cool
  7. additionNext, 1.0 g (0 5% by weight of solids) of p-toluene sulfonic acid was added
  8. temperaturethe mixture was refluxed
  9. additionA solution of 0.5 g of NaHCO3 in deionized water was then added
  10. stirringThe resulting two-phase system was stirred
  11. customthe water and toluene were removed at 80° C.
  12. customa ROTO-VAC™ evaporator

Sources & evidence

ORD record
ord-5d95c103314b44f2bbbba63577a6e9d2
Source dataset
uspto-grants-2003_03
Patent number
US06537662B1

Reaction notes

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