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

HRID 1003755Notes

Reaction equation

HRID 1003755 reaction equation
[Br:1]C1C=CC=CC=1C=O.[CH2:10]([OH:13])[CH2:11][OH:12].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17](S(O)(=O)=O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C1(C)C=CC=CC=1>[Br:1][C:17]1[CH:18]=[CH:19][C:14]([CH:24]2[O:13][CH2:10][CH2:11][O:12]2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 811292-Bromobenzaldehyde

Product 1

HCID 27738422-(4-Bromophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

40 g (216 mmol) of bromobenzaldehyde, 39 ml (700 mmol) of ethylene glycol, 1.6 g (9.3 mmol) of p-toluene sulphonic acid and 670 ml of toluene are introduced into a 2 l three-necked flask equipped with a Dean-Stark apparatus under nitrogen. The reaction mixture is taken to reflux whilst eliminating the water formed. After 24 hours of reflux, the reaction mixture is hydrolized with a saturated solution of sodium carbonate (240 ml). The organic phase is recovered and washed twice with a saturated solution of sodium chloride (2×160 ml), then concentrated under vacuum. The crude product obtained is distilled under 40 mm/Hg (150-156° C.).

Workup

  1. customequipped with a Dean-Stark apparatus under nitrogen
  2. temperatureto reflux
  3. customformed
  4. temperatureAfter 24 hours of reflux
  5. customThe organic phase is recovered
  6. washwashed twice with a saturated solution of sodium chloride (2×160 ml)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a54c1747fabe4c7894f4cb9f42347a8e
Source dataset
uspto-grants-2000_04
Patent number
US06046352

Reaction notes

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