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Glycerol → Monostearin

HRID 489057
Notes
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Reaction equation

HRID 489057 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].N1C=CC=CC=1.[C:13](Cl)(=[O:31])[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][CH2:29][CH3:30].C([O-])(O)=O.[Na+]>CN(C=O)C>[C:13]([O:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4])(=[O:31])[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][CH2:29][CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 753GlycerolHCID 1049PyridineHCID 8212Stearoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 24699Monostearin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of glycerol (30 g, 326 mmol) and pyridine (25 ml) dissolved in DMF (300 ml) was added dropwise stearoyl chloride (10 g, 33 mmol) dissolved in DMF 100 ml9. The mixture was cooled on an ice bath until addition was complete, whereupon the reaction was maintained under an N2 atmosphere overnight. After 15 hours CH2CL2 (300 ml) and saturated NaHCO3 (aq) was added. The phases were separated and the organic phase washed with water (50 ml) and dried with Na2SO4.

Workup

  1. temperatureThe mixture was cooled on an ice bath until addition
  2. temperaturewas maintained under an N2 atmosphere overnight
  3. customThe phases were separated
  4. washthe organic phase washed with water (50 ml)
  5. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-e0db80c15c0749028813e3ba995226be
Source dataset
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06974802B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes