p-Toluenesulfonic acid → HCID 70619866, compound

HRID 2398087Notes

Reaction equation

HRID 2398087 reaction equation
[Br:1][CH2:2][CH:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[OH:4].[C:10]1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:10][O:4][CH:3]([CH2:2][Br:1])[C:5]1[S:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22324999HCID 22324999, compound

Product 1

HCID 70619866HCID 70619866, compound

Procedure

A solution of the halohydrin, α-bromomethyl-2-thiophenemethanol (10.0 g, 0.048 mole), described in Example 4, and p-toluenesulfonic acid (1.0 g) in 100 ml of the lower alkanol methanol, is heated at reflux for 5 hr. The mixture is concentrated and the concentrate extracted with ether. The ether extract is washed with water and brine, dried (MgSO4) and concentrated to yield a brown liquid which is purified by chromatography on silica gel to give α-(bromomethyl)-2-thiophenemethanol methyl ether; nmr (CDCI3) δ3.36 (s, 3H), 3.58 (m, 2H), 4.68 (t, J = 6.5, 1H), 7.02 (m, 1), 7.05 (m, 1H), 7.31 (m, 1H).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 5 hr
  3. concentrationThe mixture is concentrated
  4. extractionthe concentrate extracted with ether
  5. extractionThe ether extract
  6. washis washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto yield a brown liquid which
  10. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-6aa29a79e714429491de892c6143f7a1
Source dataset
uspto-grants-1977_05
Patent number
US04024156

Reaction notes

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