Pyridine → 16-Hexadecanoyloxyhexadecanoic acid

HRID 1603972Notes

Reaction equation

HRID 1603972 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][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)(=[O:42])[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]>O1CCCC1>[C:26]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:42])[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]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8206Palmitoyl chlorideHCID 1046616-Hydroxyhexadecanoic acid

Product 1

HCID 1960674616-Hexadecanoyloxyhexadecanoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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, eluting 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): δ 0.85 (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): δ 14.01, 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. washeluting with chloroform with increasing methanol concentration (from 1% to 2% methanol in chloroform)

Sources & evidence

ORD record
ord-529f7f01d19b441bacd19d9b17fabfdc
Source dataset
uspto-grants-1999_11
Patent number
US05990263

Reaction notes

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