Ammonium Chloride → 3-(3-Methyl-2-butenyl)benzaldehyde dimethyl acetal

HRID 2254436Notes

Reaction equation

HRID 2254436 reaction equation
[Mg].[CH3:2][O:3][CH:4]([O:12][CH3:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Br)[CH:6]=1.[CH3:14][C:15]([CH3:19])=[CH:16][CH2:17]Br.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH3:2][O:3][CH:4]([O:12][CH3:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:17][CH:16]=[C:15]([CH3:19])[CH3:14])[CH:6]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 700922-Butene, 1-bromo-3-methyl-HCID 1053951-Bromo-3-(dimethoxymethyl)benzeneHCID 5462224Magnesium

Product 1

HCID 197445523-(3-Methyl-2-butenyl)benzaldehyde dimethyl acetalYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

Magnesium metal (1.2 g) was added to 2 ml of tetrahydrofuran. With stirring at room temperature, 20 ml of a solution of 2.0 g of 3-bromobenzaldehyde dimethyl acetal in a 1:1 mixture of tetrahydrofuran and ethyl ether was added dropwise over the course of 1 hour. With stirring under ice cooling, 15 ml of a tetrahydrofuran solution of 2.25 g of 3-methyl-2-butenyl bromide was added to the resulting solution. The temperature of the mixture was returned to room temperature, and then it was stirred for 1 hour. A saturated aqueous solution of ammonium chloride was added to the reaction mixture to terminate the reaction. Ethyl ether was added, and the reaction mixture was treated in a customary manner to give 1.71 g (yield 90%) of 3-(3-methyl-2-butenyl)benzaldehyde dimethyl acetal as a colorless oil.

Workup

  1. additionwas added dropwise over the course of 1 hour
  2. stirringWith stirring under ice cooling
  3. customwas returned to room temperature
  4. stirringit was stirred for 1 hour
  5. customto terminate
  6. customthe reaction
  7. additionthe reaction mixture was treated in a customary manner

Sources & evidence

ORD record
ord-043c3a80bd024068a76196ffc5ebb01b
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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