1-Bromohexadecane → HCID 13982249, compound

HRID 414770Notes

Reaction equation

HRID 414770 reaction equation
[OH:1][CH2:2][C:3]1[O:8][CH2:7][CH2:6][CH2:5][CH:4]=1.[CH2:9](Br)[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][CH3:24].[OH-].[K+]>C1(C)C=CC=CC=1>[CH2:24]([O:1][CH2:2][C:3]1[O:8][CH2:7][CH2:6][CH2:5][CH:4]=1)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9]

Participants

5

Reactant 3

HCID 82131-BromohexadecaneHCID 14797Potassium HydroxideHCID 12511647(3,4-Dihydro-2H-pyran-6-yl)methanol

Product 1

HCID 13982249HCID 13982249, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.71 g of 6-hydroxymethyl-3,4-dihydro-2H-pyran, 16.79 g of hexadecyl bromide and 8.22 g of pulverized 85% potassium hydroxide were mixed in 160 ml of toluene and heated under reflux for 2 hours. The mixtured was then cooled, washed with water, dried and condensed by evaporation under reduced pressure. The resulting oily residue, 17 g, was subjected to column chromatography through 400 g of silica gel. The fraction eluted with a 1:5 by volume mixture of diethyl ether and hexane gave 14.38 g of the title compound as a colorless oily substance.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe mixtured was then cooled
  4. washwashed with water
  5. customdried
  6. customcondensed
  7. customby evaporation under reduced pressure
  8. washThe fraction eluted with a 1:5 by volume mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-fff84678a2fd4db3877e2e494e28a446
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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