Acetyl chloride → 16-Acetoxyhexadecanoic acid

HRID 1780694Notes

Reaction equation

HRID 1780694 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].C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28].C(Cl)(Cl)Cl.CCCCCC>C(Cl)Cl>[C:27]([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:29])[CH3:28]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 1046616-Hydroxyhexadecanoic acidHCID 21585165Chloroform hexane

Product 1

HCID 1318099616-Acetoxyhexadecanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16-Hydroxyhexadecanoic acid (0.5 g) was suspended in methylene chloride (15 ml), and triethylamine (1.03 ml) was added to the suspension. To the mixture, while ice-cooled and stirred, was added dropwise acetyl chloride (0.39 ml). After 8 hours ice was added, and extracted with chloroform. The chloroform layer was washed with a saturated sodium hydrogen carbonate solution and then twice with water and dried with anhydrous sodium sulfate. The chloroform layer was concentrated and the residue thus obtained was subjected to chromatography on a silica gel column with an eluent system of chloroform-hexane (2:1) to give 16-acetoxyhexadecanoic acid (0.58 g).

Workup

  1. temperatureTo the mixture, while ice-cooled
  2. additionAfter 8 hours ice was added
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with a saturated sodium hydrogen carbonate solution
  5. dry with materialtwice with water and dried with anhydrous sodium sulfate
  6. concentrationThe chloroform layer was concentrated
  7. customthe residue thus obtained

Sources & evidence

ORD record
ord-1e93ac3fa27743078cd5a56e9337c88b
Source dataset
uspto-grants-1997_05
Patent number
US05631238

Reaction notes

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