3-Hydroxybenzaldehyde → 3-(1,3-Dioxolan-2-yl)phenol

HRID 1200255Notes

Reaction equation

HRID 1200255 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10](O)[CH2:11][OH:12]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:6]1[CH2:10][CH2:11][O:12][CH:5]1[C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([OH:1])[CH:3]=1

Participants

5

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 174Ethylene Glycol

Product 1

HCID 132801193-(1,3-Dioxolan-2-yl)phenolYield 64.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 3-hydroxybenzaldehyde (91.6 g, 0.75 mol) in 500 ml toluene is added ethylene glycol (333.0 g, 5.3 mol) and p-toluenesulfonic acid (0.19 g, 0.001 mol). The flask is equipped with a Dean-Stark trap and the mixture is refluxed for 2 days, extracted with saturated sodium bicarbonate solution and the organic phase separated and dried (MgSO4). Filtration and evaporation of solvent gives the title product as an oil (80.3 g, 64% yield).

Workup

  1. customThe flask is equipped with a Dean-Stark trap
  2. temperaturethe mixture is refluxed for 2 days
  3. extractionextracted with saturated sodium bicarbonate solution
  4. customthe organic phase separated
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-71e44558e9fe41409ca2b034997d6a92
Source dataset
uspto-grants-1990_02
Patent number
US04904786

Reaction notes

Loading…