Water → 2-Acetoxyhexadecanoic acid

HRID 1780695Notes

Reaction equation

HRID 1780695 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([OH:5])=[O:4].[C:20](OC(=O)C)(=[O:22])[CH3:21].C(Cl)(Cl)Cl.O>N1C=CC=CC=1>[C:20]([O:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([OH:5])=[O:4])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 928362-Hydroxyhexadecanoic acid

Product 1

HCID 155995342-Acetoxyhexadecanoic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Hydroxyhexadecanoic acid (1 g) was dissolved in pyridine, and acetic anhydride (0.62 g) was added to the solution in an ice bath. After 12 hours, the reaction mixture was distributed into chloroform and water, and the chloroform layer was concentrated to give 2-acetoxyhexadecanoic acid (1.10 g). To 2-acetoxyhexadecanoic acid (0.50 g) dissolved in N,N-dimethylformamide (DMF) were added para-nitrophenol (0.22 g) and N,N'-dicyclohexylcarbodiimide (0.33 g), and the mixture was stirred for 8 hours. The reaction mixture was filtered, and 6-(4'-N-glycyl-spicaminyl-amino)purine hydrochloride (0.61 g) and triethylamine (2.0 ml) were added to the filtrate. The mixture was stirred for 12 hours.

Workup

  1. concentrationthe chloroform layer was concentrated

Sources & evidence

ORD record
ord-6d1645b6472e47a08201eab66c1285e7
Source dataset
uspto-grants-1997_05
Patent number
US05631238

Reaction notes

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