Acetic Acid → Octadecanoic acid--hex-2-ulofuranosyl hexopyranoside (1/1)

HRID 2400138Notes

Reaction equation

HRID 2400138 reaction equation
[CH2:1]([OH:23])[C@H:2]1[O:7][C@H:6]([O:8][C@:9]2([CH2:18][OH:19])[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@@H:10]2[OH:17])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[C:24]([O:43]C)(=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].C(O)(=O)C>CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>[CH3:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:24]([OH:43])=[O:42].[CH2:1]([OH:23])[CH:2]1[O:7][CH:6]([O:8][C:9]2([CH2:18][OH:19])[O:13][CH:12]([CH2:14][OH:15])[CH:11]([OH:16])[CH:10]2[OH:17])[CH:5]([OH:20])[CH:4]([OH:21])[CH:3]1[OH:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5988SucroseHCID 8201Methyl Stearate

Product 1

HCID 303618Octadecanoic acid--hex-2-ulofuranosyl hexopyranoside (1/1)Yield 75.8%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 6228DimethylformamideSolvent

Procedure

In 4 l of dimethylformamide was dissolved 1 kg (2.93 mols) of sucrose at 90° C., followed by addition of 10 g of potassium carbonate and 600 g (2 mols) of methyl stearate, and the mixture was reacted under a reduced pressure of 70-90 mmHg at 90° C. for 3 hours. Then, 8 ml of acetic acid was added and the solvent was removed under reduced pressure. The residue was dissolved in 5 l of methyl ethyl ketone and the solution was washed with 3 portions of water. The methyl ethyl ketone was then removed under reduced pressure and the residue was recrystallized from acetone to provide 950 g of sucrose stearic acid ester.

Workup

  1. customthe mixture was reacted under a reduced pressure of 70-90 mmHg at 90° C. for 3 hours
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in 5 l of methyl ethyl ketone
  4. washthe solution was washed with 3 portions of water
  5. customThe methyl ethyl ketone was then removed under reduced pressure
  6. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-5b0a3f03b202499e87343b1d972445fc
Source dataset
uspto-grants-1995_09
Patent number
US05453498

Reaction notes

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