Ethylene Glycol → 2-(4-Bromophenyl)-1,3-dioxolane

HRID 1387702Notes

Reaction equation

HRID 1387702 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][OH:12]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:12][CH2:11][CH2:10][O:7]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 707414-Bromobenzaldehyde

Product 1

HCID 27738422-(4-Bromophenyl)-1,3-dioxolaneYield 23,613.199%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 4-bromobenzaldehyde (5 g, 0.027 mol), ethylene glycol (7.0 g, 0.11 mmol), and p-toluenesulfonic acid (0.1 g, 0.5 mmol) in benzene was heated at reflux for 24 h using a Dean-Stark setup to remove water. The reaction was taken up in diethyl ether (100 mL) and washed with water (5×30 mL) and brine (30 mL). The organic phase was dried over magnesium sulfate and concentrated under vacuum to afford 2-(4′-bromophenyl)-1,3-dioxolane (5.95 g).

Workup

  1. temperatureat reflux for 24 h
  2. customto remove water
  3. washwashed with water (5×30 mL) and brine (30 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-608781426b45460a933b29f9937cb07c
Source dataset
uspto-grants-2001_07
Patent number
US06268513B1

Reaction notes

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