Ethylene Glycol → Methyl 3-(1,3-dioxolan-2-yl)benzoate

HRID 1198548Notes

Reaction equation

HRID 1198548 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[CH2:13]([OH:16])[CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[O:15]1[CH2:14][CH2:13][O:16][CH:1]1[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 639145Methyl 3-formylbenzoate

Product 1

HCID 19102594Methyl 3-(1,3-dioxolan-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of methyl 3-formylbenzoate (10.0 g., 61 mmol), ethylene glycol (5.0 ml, 91 mmol) and p-toluene sulphonic acid (10 mb) in toluene (100 ml) was refluxed under a Dean and Stark water trap for 4 hours. The cooled solution was washed with sodium bicarbonate solution, dried and evaporated to a pale oil.

Workup

  1. washThe cooled solution was washed with sodium bicarbonate solution
  2. customdried
  3. customevaporated to a pale oil

Sources & evidence

ORD record
ord-372c90a64fd245fd86259c3a0004d12d
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

Loading…