Acetic Anhydride → 2-Acetyloxy-1-benzyloxy-3-hexadecyloxybutane

HRID 2081517Notes

Reaction equation

HRID 2081517 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:30])[CH:11]([O:13][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][CH3:29])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:31]([O:30][CH:10]([CH:11]([O:13][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][CH3:29])[CH3:12])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 150522931-Benzyloxy-3-hexadecyloxy-2-butanol

Product 1

HCID 150522942-Acetyloxy-1-benzyloxy-3-hexadecyloxybutaneYield 95.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In chloroform, 4.33 g of 1-benzyloxy-3-hexadecyloxy-2-butanol, 26.34 g of acetic anhydride and 10.42 g of triethylamine were heated under reflux for 17 hours. The reaction mixture was treated in a conventional manner and purified by silica gel column chromatography to give 4.56 g of 2-acetyloxy-1-benzyloxy-3-hexadecyloxybutane.

Workup

  1. temperatureunder reflux for 17 hours
  2. additionThe reaction mixture was treated in a conventional manner
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-328f688d293640b4b7cd121287ffca28
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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