Allyl bromide → 3-(Prop-2-en-1-yl)benzaldehyde

HRID 462445Notes

Reaction equation

HRID 462445 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Mg].[CH2:11](Br)[CH:12]=[CH2:13].[Cl-].[NH4+]>C1COCC1.C(=O)=O>[CH2:13]([C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH:12]=[CH2:11]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 765833-BromobenzaldehydeHCID 5462224Magnesium

Product 1

HCID 220226903-(Prop-2-en-1-yl)benzaldehydeYield 101.3%

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The ethylene acetal of 3-bromobenzaldehyde (10 g) is converted into the Grignard reagent by reaction with magnesium (1.13 g) in dry THF (ca. 250 ml). Cuprous bromide (0.9 g) is added and the mixture is cooled in cardice. Allylbromide (8.52 g) in dry THF is then added and the mixture is stirred overnight following which saturated ammonium chloride is added, the mixture is extracted with diethyl ether (3 times), the ether extract is washed, dried and the solvent evaporated to yield the crude ethylene acetal of 3-allylbenzaldehyde (8 g).

Workup

  1. additionis added
  2. extractionthe mixture is extracted with diethyl ether (3 times)
  3. extractionthe ether extract
  4. washis washed
  5. customdried
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-6aae9a641d6640b5a687d8b7d3b7c259
Source dataset
uspto-grants-1985_05
Patent number
US04515808

Reaction notes

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