p-Toluenesulfonic acid → 8-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

HRID 1707242Notes

Reaction equation

HRID 1707242 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:17][CH2:16][C:11]3([O:12][CH2:13][CH2:14][O:15]3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 152326818-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 152326828-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-eneYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol (2.0 g, 7.9 mmole) and a catalytic amount of p-toluenesulfonic acid in 50 ml toluene was heated at reflux for 1.5 hr. The mixture was cooled and washed with saturated sodium bicarbonate solution. The toluene was removed in vacuo and the residue recrystallized from hexane to give the product (81%, mp: 84°-85° C). Calc'd for C14H15FO2 : C, 71.78%; H, 6.46%. Found: C, 71.33%; H, 6.33%.

Workup

  1. temperatureat reflux for 1.5 hr
  2. temperatureThe mixture was cooled
  3. washwashed with saturated sodium bicarbonate solution
  4. customThe toluene was removed in vacuo
  5. customthe residue recrystallized from hexane

Sources & evidence

ORD record
ord-fd9de30b1d364045a9a5374d2ebf50c9
Source dataset
uspto-grants-1994_10
Patent number
US05352678

Reaction notes

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