Benzyl Chloride → 3-Butenylbenzene

HRID 1108037Notes

Reaction equation

HRID 1108037 reaction equation
[CH2:1]([Mg]Cl)[CH:2]=[CH2:3].C(Cl)C=C.[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1.C1(C)C=CC=CC=1>[C:11]1([CH2:10][CH2:3][CH:2]=[CH2:1])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 7850Allyl chlorideHCID 178418473HCID 178418473, compound

Product 1

HCID 130333-ButenylbenzeneYield 90%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

Example 8 was repeated to form allyl magnesium chloride. The allyl magnesium chloride which flowed out of the flask through the branch was accumulated in a 3 L four-necked flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel placed under a nitrogen atmosphere. A mixed solvent of toluene and tetrahydrofuran dissolving allyl chloride was started to be added dropweise thereto. 2 hours after the start of the addition of the mixed solvent, 300 ml of a mixed solvent of toluene and tetrahydrofuran (a content of terahydrofuran 25% by weight) dissolving 156 g (1.23 mole) of benzyl chloride was added dropwise in the 3 L four-necked flask at a rate of 15 ml per hour at a temperature of 0 to 20° C. After the completion of the dropwise addition, the reaction mixture was stirred for 1 hour at the same temperature. After the completion of the reaction, an aftertreatment was effected in a similar manner to that in Example 1 to obtain 146.9 g (yield 90%, based on benzyl chloride) of 4-phenyl-1-butene which was a colorless liquid. An analysis of the product by gas chromatography indicated the purity of 98.7%.

Workup

  1. customwas accumulated in a 3 L four-necked flask
  2. customequipped with a stirrer
  3. additionto be added dropweise
  4. additionwas added dropwise in the 3 L four-necked flask at a rate of 15 ml per hour at a temperature of 0 to 20° C
  5. additionAfter the completion of the dropwise addition
  6. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-5f4e0ca85aa94e8c884d7bcaaae20082
Source dataset
uspto-grants-2000_05
Patent number
US06063940

Reaction notes

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