Ethylene Glycol → 8-(3-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

HRID 1106374Notes

Reaction equation

HRID 1106374 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.C1(C)C(C)=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)CO>O>[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 7237O-XyleneHCID 18787929HCID 18787929, compound

Product 1

HCID 187879328-(3-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

513 g of 8-(3-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol, 1.8 l of xylene, 19 g of p-toluenesulfonic acid and 50 ml of ethylene glycol were boiled for 4 hours in a water separator. The reaction solution was cooled to room temperature and washed with 2×200 ml of water. The organic extracts were dried using sodium sulfate, filtered and evaporated to a residue, giving 8-(3-fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene.

Workup

  1. washwashed with 2×200 ml of water
  2. customThe organic extracts were dried
  3. filtrationfiltered
  4. customevaporated to a residue

Sources & evidence

ORD record
ord-05d422199df34f24a2bf5ef275666202
Source dataset
uspto-grants-2000_05
Patent number
US06057006

Reaction notes

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