Ethylene Glycol → 4-Bromo-3-(1,3-dioxolan-2-yl)phenol

HRID 1471469Notes

Reaction equation

HRID 1471469 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](O)[CH2:12][OH:13]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]1[O:13][CH2:12][CH2:11][O:5]1

Participants

6

Reactant 2

HCID 174Ethylene GlycolHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 579687074-Bromo-3-(1,3-dioxolan-2-yl)phenolYield 90.2%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 11430Potassium CarbonateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-5-hydroxybenzaldehyde (60.0 g, 299 mmol), ethylene glycol (56 mL, 1.00 mol), and p-toluenesulfonic acid (1.14 g, 5.98 mmol) in toluene (450 mL) was refluxed with Dean-Stark head for overnight. Potassium carbonate (3 g) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 4-bromo-3-(1,3-dioxolan-2-yl)phenol (66.1 g, 90%).

Workup

  1. temperaturewas refluxed with Dean-Stark head for overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-80814de80d8d4306b3d87baadca950f1
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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