Pyridine → Benzoyloxymethyl chloroformate

HRID 1488352Notes

Reaction equation

HRID 1488352 reaction equation
OCCCCCCCCC[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].N1C=CC=CC=1.[C:26]([Cl:43])(=[O:42])CCCCCCCCCCCCCCC.[O:44]1CCC[CH2:45]1>>[Cl:43][C:26]([O:44][CH2:45][O:19][C:17](=[O:18])[C:16]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:42]

Participants

5

Reactant 4

HCID 1049PyridineHCID 8028Tetrahydrofuran2×HCID 8206Palmitoyl chlorideHCID 1046616-Hydroxyhexadecanoic acid

Product 1

HCID 14800986Benzoyloxymethyl chloroformateYield 83%

Procedure

16-Hydroxyhexadecanoic acid (5.43 g, 19.9 mmol) was dissolved in tetrahydrofuran (190 ml) and pyridine (2.36 g, 29.9 mmol) was added. Palmitoyl chloride (5.48 g, 19.9 mmol) was dissolved in tetrahydrofuran (10 ml) and added dropwise at room temperature. After stirring at room temperature for 16 hours, the mixture was filtered and the filtrate evaporated under reduced pressure. The residue was dissolved in chloroform, washed with water (3×50 ml), and the organic phase was dried (MgSO4). After evaporating under reduced pressure, the residue was purified on a silica column, eluted with chloroform with increasing methanol concentration (from 1% to 2% methanol in chloroform) to give 8.41 g (83%) of the title compound. 1H NMR (300 MHz, CDCl3): δ0.85 (t, 3H, CH3), 1.20-1.35 (s, 46H, --CH2 --), 1.55-1.70 (m, 6H, --CH2 --), 2.25 (t, 2H, --CH2 --C(O)--O), 2.45 (t, 2H, --CH2 --COOH), 4.05 (t, 2H, --O--CH2). 13C NMR (75 MHz, CDCl3): δ14.01, 22.57, 24.10, 24.91, 25.82, 28.53, 28.75, 28.94, 29.08, 29.15, 29.25, 29.36, 29.54, 31.81, 34.29, 35.16, 64.27, 76.48, 76.90, 77.10, 77.32, 169.50, 173.91.

Workup

  1. additionadded dropwise at room temperature
  2. filtrationthe mixture was filtered
  3. customthe filtrate evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with water (3×50 ml)
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customAfter evaporating under reduced pressure
  8. customthe residue was purified on a silica column
  9. washeluted with chloroform with increasing methanol concentration (from 1% to 2% methanol in chloroform)

Sources & evidence

ORD record
ord-bd0f1720b60048a98fb0f41fd6588cb9
Source dataset
uspto-grants-1997_10
Patent number
US05674468

Reaction notes

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