Methyl Stearate → [2-[(2R,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] octadecanoate

HRID 2195001Notes

Reaction equation

HRID 2195001 reaction equation
[CH2:1]1[O:5][CH:4]([CH:6]([OH:9])[CH2:7][OH:8])[C@@H:3]([OH:10])[CH:2]1[OH:11].[C:12](OC)(=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].CO.C[O-].[Na+].[PH2]([O-])=O.[Na+]>>[CH3:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]([O:8][CH2:7][CH:6]([OH:9])[C@H:4]1[O:5][CH2:1][C@H:2]([OH:11])[C@H:3]1[OH:10])=[O:30]

Participants

5

Reactant 4

HCID 8201Methyl Stearate2×HCID 103023(3S)-2-(1,2-dihydroxyethyl)oxolane-3,4-diolHCID 23694274Sodium methanolate methanolHCID 178527019HCID 178527019, compound

Product 1

HCID 13267937[2-[(2R,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] octadecanoate

Conditions

Temperature
65 °C

Procedure

After 469 g of a 70% by weight sorbitan aqueous solution (aldehyde value of sorbitan: 7.4 ppm) and 872 g of methyl stearate were charged into a 2000 mL four-neck flask fitted with a stirring apparatus, a thermometer, and a nitrogen gas inlet, dehydration was performed at 110° C. under a nitrogen stream at normal pressure for 1 hour and further at 110° C. under a nitrogen stream at 4 kPa for 1 hour. The whole was cooled to 65° C. and, after 30.0 g of a 20% by weight sodium methoxide methanol solution and 0.06 g of sodium hypophosphite were added thereto, was heated under a nitrogen stream at normal pressure to 190° C. as a reaction temperature. After the temperature reached 190° C., pressure was reduced to 6.5 kPa and the reaction was carried out under a nitrogen stream. At the time point when the spot of methyl stearate as a raw material disappeared on thin-layer chromatography, it was judged that the reaction was completed. The reaction time was 5 hours and, after the completion of the reaction was confirmed, the mixture was filtrated at 80° C. to obtain sorbitan monostearate.

Workup

  1. customfitted with a stirring apparatus
  2. customwas performed at 110° C. under a nitrogen
  3. customfor 1 hour
  4. temperaturewas heated under a nitrogen stream at normal pressure to 190° C. as a reaction temperature
  5. customreached 190° C.
  6. waitThe reaction time was 5 hours
  7. filtrationthe mixture was filtrated at 80° C.

Sources & evidence

ORD record
ord-7d7e031f939d4b6980838052f25347cd
Source dataset
uspto-grants-2012_12
Patent number
US08334397B2

Reaction notes

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