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

HRID 234618Notes

Reaction equation

HRID 234618 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-38f2e0f36c1745f48d2b7b0d1b165a03
Source dataset
uspto-grants-1997_01
Patent number
US05595993

Reaction notes

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