p-Toluenesulfonic acid → HCID 19047524, compound

HRID 742496Notes

Reaction equation

HRID 742496 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([C:10]2[CH:14]=[CH:13][O:12][CH:11]=2)(O)[CH2:7][CH3:8])=[CH:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:1]1[CH:5]=[CH:4][C:3]([C:6]([C:10]2[CH:14]=[CH:13][O:12][CH:11]=2)=[CH:7][CH3:8])=[CH:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19047542HCID 19047542, compound

Product 1

HCID 19047524HCID 19047524, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1,1-di(3-furyl)propanol (43 g) and 1 g of p-toluenesulfonic acid in 300 ml of toluene was allowed to react at room temperature and the resulting mixture was concentrated in vacuo. The residual red oil was purified by silica gel column chromatography (methylene chloride) and kugelrohr distillation (50°-80° C. at 0.25 mmHg) to afford 4 g of 1,1-di(3-furyl)-1-propene (Formula III: R3 =CH3 ; R4 =H; R5 =R6 =3-furyl) as an oil, b.p. 50°-80° C. (0.25 mm).

Workup

  1. customto react at room temperature
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. distillationThe residual red oil was purified by silica gel column chromatography (methylene chloride) and kugelrohr distillation (50°-80° C. at 0.25 mmHg)

Sources & evidence

ORD record
ord-2959e8995aad4f6caeedfde7f713069a
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

Loading…