tert-BUTYL CHLORIDE → Tert-butylcyclopentadiene

HRID 1390252Notes

Reaction equation

HRID 1390252 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.C[Al]C.[C:9](Cl)([CH3:12])([CH3:11])[CH3:10]>ClC1C=CC=CC=1>[C:9]([C:2]1[CH2:1][CH:5]=[CH:4][CH:3]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 10486tert-BUTYL CHLORIDEHCID 86736283HCID 86736283, compound

Product 1

HCID 633714Tert-butylcyclopentadiene

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

In runs 1 through 10, five ml. of 0.025M dimethylaluminum cyclopentadiene (Me2AlCPD) in chlorobenzene was dispensed by pipette into 20 × 150 mm test tubes. The tubes were then capped with screw caps fitted with self-sealing gaskets and TeflonR liners. The reaction tubes were placed in a constant temperature bath. After allowing sufficient time for the tubes and contents to attain bath temperature, 0.12 M tert.-butyl chloride solution in chlorobenzene (tBuCl) already at bath temperature was added by syringe fitted with hypodermic needle. After the desired time, the reactions were quenched by the addition of normal-butyl alcohol.

Workup

  1. customThe tubes were then capped with screw caps
  2. customfitted with self-sealing gaskets and TeflonR liners
  3. customThe reaction tubes
  4. customwere placed in a constant temperature bath
  5. additionwas added by syringe
  6. customfitted with hypodermic needle
  7. customAfter the desired time, the reactions were quenched by the addition of normal-butyl alcohol

Sources & evidence

ORD record
ord-194f707d5b794870a7cf1923a730a25c
Source dataset
uspto-grants-1979_02
Patent number
US04138441

Reaction notes

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