1-Bromohexadecane → Cetyltriethylammonium bromide

HRID 1486426

Reaction equation

HRID 1486426 reaction equation
[CH2:1]([Br:17])[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].COC(C)CO.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25]>>[Br-:17].[CH2:1]([N+:26]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:24][CH3:25])[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 3

HCID 82131-BromohexadecaneHCID 8471TriethylamineHCID 148462-Methoxy-1-propanol

Product 1

HCID 83337Cetyltriethylammonium bromide

Conditions

Temperature
75 °C

Procedure

Into a 2 L round-bottom flask was placed hexadecyl bromide (250 g), 2-methoxypropanol (250 mL), and triethylamine (200 mL). The flask was heated without stirring at 75° C. for 96 h and the contents were concentrated on a Rotavap at 75° C. and 20 mbar. To the residue, methyl tert-butyl ether (800 mL) was added. The slurry was vigorously stirred by a mechanical stirrer for 12 h, filtered, washed with 3 portions (400 mL each) of methyl tert-butyl ether, and dried in vacuum to obtain the product as a white solid in nearly quantitative yield.

Workup

  1. customInto a 2 L round-bottom flask was placed
  2. temperatureThe flask was heated
  3. concentrationthe contents were concentrated on a Rotavap at 75° C.
  4. additionTo the residue, methyl tert-butyl ether (800 mL) was added
  5. stirringThe slurry was vigorously stirred by a mechanical stirrer for 12 h
  6. filtrationfiltered
  7. washwashed with 3 portions (400 mL each) of methyl tert-butyl ether
  8. customdried in vacuum

Sources & evidence

ORD record
ord-0b045545a2a040428890c9c9319df889
Source dataset
uspto-grants-2016_08
Patent number
US09427406B2

Linked notes

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