1-Bromohexadecane → 2-(Hexadecyloxy)thiophene

HRID 328373Notes

Reaction equation

HRID 328373 reaction equation
[S:1]1[CH2:5][CH:4]=[CH:3][C:2]1=[O:6].Br[CH2:8][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][CH3:23].[H-].[Na+]>C1C=CC=CC=1>[CH2:23]([O:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[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][CH2:9][CH3:8]

Participants

5

Reactant 3

HCID 82131-BromohexadecaneHCID 24758Sodium hydrideHCID 1378982(5H)-Thiophenone

Product 1

HCID 214418272-(Hexadecyloxy)thiophene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 20 g (0.2 mole) of 3-thiolen-2-one [R.T. Hawkins, Journal Heterocyclic Chemistry, 11, (3), 291-4 (1974)], 61.1 g (0.2 mole) of 1-bromohexadecane, and 4.8 g (0.2 mole) of sodium hydride in dry benzene is refluxed with stirring for 24 hours after which the solvent is removed and the product distilled to give 2-hexadecyloxythiophene.

Workup

  1. temperatureis refluxed
  2. customis removed
  3. distillationthe product distilled

Sources & evidence

ORD record
ord-f323ec51fe0447d0914ec4186b613057
Source dataset
uspto-grants-1977_04
Patent number
US04017514

Reaction notes

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