Toluene → 1,3-Dioxolane, 2-methyl-4-phenyl-

HRID 347618

Reaction equation

HRID 347618 reaction equation
[C:1]1([CH:7]([OH:10])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1(C)C=CC=C[CH:12]=1.CC1OC(C)OC(C)O1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH3:11][CH:12]1[O:10][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][O:9]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 71491-Phenyl-1,2-ethanediolHCID 31264Paraldehyde

Product 1

HCID 1181191,3-Dioxolane, 2-methyl-4-phenyl-Yield 85.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

100 g (0.63 mol) of (±)-1-phenyl-1,2-ethanediol (3) (87% pure according to GC) according to Example 1, 200 ml of toluene, 32 g (0.24 mol) of paraldehyde and 1 g of para-toluenesulfonic acid were charged to a 1 l stirrer, heated to boiling (110° C.) and stirred under reflux for a period of 4 h. A total of 10 ml of water were eliminated. After this time, the mixture was cooled to 20° C. and washed until neutral with sodium carbonate solution and water, and the solvent was distilled off under reduced pressure, leaving 103 g of crude product (85.3% pure according to GC). GC conditions see Example 2.

Workup

  1. additionwere charged to a 1 l stirrer
  2. temperatureheated
  3. custom(110° C.)
  4. temperatureunder reflux for a period of 4 h
  5. washwashed until neutral with sodium carbonate solution and water
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-794f4d0144e84dccaef656b3b1c84b40
Source dataset
uspto-grants-2007_02
Patent number
US07176176B2

Linked notes

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