Benzene → HCID 23466138, compound

HRID 444061Notes

Reaction equation

HRID 444061 reaction equation
Cl.[CH2:2]([O:18][CH2:19][CH:20]([CH2:26][O: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][CH2:41][CH2:42][CH3:43])[O:21][CH2:22][CH2:23][CH2:24][NH2:25])[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][CH3:17].C(=O)([O-])[O-].[K+].[K+].C1C=CC=CC=1.[C:56](Cl)(=[O:58])[CH3:57]>O>[CH2:2]([O:18][CH2:19][CH:20]([CH2:26][O: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][CH2:41][CH2:42][CH3:43])[O:21][CH2:22][CH2:23][CH2:24][NH:25][C:56](=[O:58])[CH3:57])[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][CH3:17]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6367Acetyl chloride2×HCID 11430Potassium CarbonateHCID 23466108HCID 23466108, compound

Product 1

HCID 23466138HCID 23466138, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-Di-O-(n-hexadecyl)-2-O-(3-aminopropyl)-glycerol hydrochloride (1.0 g., 1.6 mmoles) was added to a mixture of potassium carbonate (830 mg., 6.0 mmoles) and benzene (75 ml.). Acetyl chloride (150 mg., 1.9 mmoles) was then added and the resulting mixture stirred for one hour at reflux. Additional acetyl chloride (150 mg., 1.9 moles) was added and the reaction mixture stirred for another hour at reflux. TLC analysis showed that the reaction was essentially complete. The reaction mixture was cooled, water (75 ml.) added, and the resulting mixture extracted with ether (3×100 ml.). The combined ether extract was dried (MgSO4), filtered and evaporated in vacuo to yield the named compound [800 mg., 79% yield, m.p. 53°-54° C., ir (CHCl3) 3400 and 1670 cm-1, n.m.r. (CDCl3) δ 1.97 (s, 3, --NHCOCH3)].

Workup

  1. temperatureat reflux
  2. stirringthe reaction mixture stirred for another hour
  3. temperatureat reflux
  4. temperatureThe reaction mixture was cooled
  5. extractionthe resulting mixture extracted with ether (3×100 ml.)
  6. extractionThe combined ether extract
  7. dry with materialwas dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto yield the named compound [800 mg., 79% yield, m.p. 53°-54° C., ir (CHCl3) 3400 and 1670 cm-1, n.m.r. (CDCl3) δ 1.97 (s, 3, --NHCOCH3)]

Sources & evidence

ORD record
ord-08a7354746d440e3bf36a2d8ef0d9a27
Source dataset
uspto-grants-1981_04
Patent number
US04262021

Reaction notes

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