Glycerol → Monostearin

HRID 1790809Notes

Reaction equation

HRID 1790809 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]

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 Na2 SO4. The solvent and any pyridine were evaporated under vacuum. The crude product was chromatographed on a silica column (CH2Cl2-MeOH, 20:1) and recrystallised (CH2Cl2-ether) to yield around 7 grams.

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. customdried with Na2 SO4
  6. customThe solvent and any pyridine were evaporated under vacuum
  7. customThe crude product was chromatographed on a silica column (CH2Cl2-MeOH, 20:1)
  8. customrecrystallised (CH2Cl2-ether)
  9. customto yield around 7 grams

Sources & evidence

ORD record
ord-2119ae9c18764cd0b63e1aeb09c79fef
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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