1-Bromooctadecane → 3-Hydroxy-2-methoxypropyl octadecylcarbamate

HRID 1608029Notes

Reaction equation

HRID 1608029 reaction equation
[CH3:1][O:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].[CH2:8](Br)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[O-:27][C:28]#[N:29].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.C(Cl)Cl>[CH2:8]([NH:29][C:28]([O:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:6][OH:7])=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 3

HCID 82181-BromooctadecaneHCID 111709312-Methoxypropane-1,3-diolHCID 11378442Potassium cyanate

Product 1

HCID 132057943-Hydroxy-2-methoxypropyl octadecylcarbamate

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2.12 g (20 mmol) of 2-methoxy-1,3-propanediol 7.99 g (24 mmol) of octadecyl bromide, 2.43 g (30 mmol) of potassium cyanate and 1.29 g (4 mmol) of tetrabutyl ammonium bromide in 100 ml of dry acetonitrile was refluxed with stirring, at 100° C. for 24 hours. The resultant mixture was then diluted with hot methylene chloride, filtered and the filtrate concentrated in vacuo. The crude product was then purified by flash silica gel chromatography employing a mixture of petroleum ether and ethyl acetate in a 4:1 ratio as the eluent to yield the title compound as a solid, m.p. 56°-58° C.

Workup

  1. temperaturewas refluxed
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe crude product was then purified by flash silica gel chromatography
  5. additiona mixture of petroleum ether and ethyl acetate in a 4:1 ratio as the eluent

Sources & evidence

ORD record
ord-0b02e260b7744098b62d1fc87e0da2ab
Source dataset
uspto-grants-1989_09
Patent number
US04868319

Reaction notes

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