Myristyl bromide → 3-(Tetradecyloxy)benzenemethanol

HRID 484304

Reaction equation

HRID 484304 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5]CO.Br[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].[OH-:26].[Na+]>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.C1(C)C=CC=CC=1>[CH2:12]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][OH:26])[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

6

Reactant 3

HCID 8208Myristyl bromideHCID 14798Sodium HydroxideHCID 834043-Hydroxyphenethyl alcohol

Product 1

HCID 100417103-(Tetradecyloxy)benzenemethanolYield 652.2%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 66 g of 3-hydroxyphenethyl alcohol, 147.43 g of 1-bromotetradecane, 27.65 g of sodium hydroxide and 2.15 g of trioctylmethyl ammonium chloride in 400 ml of toluene was refluxed for 42 hours. The mixture was washed with water and the organic layer dried with magnesium sulfate. The solvent was removed in vacuo and the warm concentrate poured into 1 liter of hexanes. The resulting solid was washed with cold hexanes then dried giving 998.6 g of the desired compound as a white solid.

Workup

  1. temperaturewas refluxed for 42 hours
  2. washThe mixture was washed with water
  3. dry with materialthe organic layer dried with magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. concentrationthe warm concentrate
  6. additionpoured into 1 liter of hexanes
  7. washThe resulting solid was washed with cold hexanes
  8. customthen dried

Sources & evidence

ORD record
ord-1161c2df0c8046888a26a9778defb941
Source dataset
uspto-grants-1993_07
Patent number
US05231091

Linked notes

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