Acetic Anhydride → 3-Hexadecyloxy-2-acetoxymethylpropan-1-ol

HRID 34300Notes

Reaction equation

HRID 34300 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:22][O:23][C:24]([C:37]1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:20][OH:21])[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][CH3:16].C(OC(=O)C)(=[O:45])C>N1C=CC=CC=1>[CH2:1]([O:17][CH2:18][CH:19]([CH2:22][O:23][C:24](=[O:45])[CH3:37])[CH2:20][OH:21])[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][CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 212991503-Hexadecyloxy-2-triphenylmethoxymethylpropan-1-ol

Product 1

HCID 212991643-Hexadecyloxy-2-acetoxymethylpropan-1-olYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of compound 4 (2.80 g, 4.90 mmol) in acetic anhydride (5 ml) and pyridine (5 ml) was stirred at room temperature for 6 hours. The solution was concentrated and the oil was dissolved in 4:3:1 glacial acetic acid-ethanol-water (20 ml) and heated on a steam bath. After 2 hours the solution was concentrated and the residue was chromatographed on silica gel using 10% ethylacetatehexane to afford 1.53 g (84%) of the title compound (6) as a waxy white solid, m.p. 33°. NMR (CDCl3, (CH3)4Si); δ0.90 (t, 3H, J=6 Hz, --CH3), 1.25 (s, 26H, --CH2 --), 1.54 (m, 2H, --OCH2CH2R), 2.03 (s, 3H, CH3), 2.16 (m, 1H, CH), 2.54 (t, 1H, J=6.5 Hz, --OH), 3.41 (t, 3H, J=6.5 Hz, --OCH2R), 3.53, 3.56 (ABX, 2H, JAB =8.5, /J 5 Hz, --CH2OR), 3.73 (t, 2H, J=5 Hz, CH2OH), 4.18 (d, 2H, J=6.5 Hz, CH2OAc).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe oil was dissolved in 4:3:1 glacial acetic acid-ethanol-water (20 ml)
  3. temperatureheated on a steam bath
  4. concentrationAfter 2 hours the solution was concentrated
  5. customthe residue was chromatographed on silica gel using 10% ethylacetatehexane

Sources & evidence

ORD record
ord-73abe1fc001642bfaa0e5b2186c427e9
Source dataset
uspto-grants-1988_08
Patent number
US04761404

Reaction notes

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