Hydrochloric Acid → 3-tert-Butyl-1-methylcyclopenta-1,3-diene

HRID 1361564Notes

Reaction equation

HRID 1361564 reaction equation
[CH3:1][Mg]Br.[C:4]([C:8]1[CH2:12][CH2:11][C:10](=O)[CH:9]=1)([CH3:7])([CH3:6])[CH3:5].Cl>C(OCC)C>[CH3:1][C:11]1[CH2:10][CH:9]=[C:8]([C:4]([CH3:7])([CH3:6])[CH3:5])[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 119769972-Cyclopenten-1-one, 3-(1,1-dimethylethyl)-HCID 178418573HCID 178418573, compound

Product 1

HCID 153463033-tert-Butyl-1-methylcyclopenta-1,3-diene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a 500 ml three-neck flask equipped with a magnetic stirrer chip and a three-way cock, 100 ml of dehydrated diethyl ether and 57 ml (170 mmol) of diethyl ether solution of 3.0 M methyl magnesium bromide were charged under a nitrogen atmosphere. In the ice bath, 19.6 g (142 mmol) of 3-tert-butylcyclopentenone was added dropwise over 1 hour. The resultant solution was stirred at room temperature for 20 hours, and then the reaction solution was poured into 100 ml of 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with 50 ml of ether. The obtained organic layers were combined, washed twice with a saturated aqueous solution of sodium hydrogencarbonate, twice with water, and twice with saturated brine and dried over magnesium sulfate and the solvent was distilled off. Thereafter, the purification was conducted by distillation under reduced pressure to obtain 13.5 g of a pale yellowy transparent liquid. The yield constant was 70%. Identification was done by 1H-NMR spectrum. The measurement results are shown as follows.

Workup

  1. customTo a 500 ml three-neck flask equipped with a magnetic stirrer chip
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with 50 ml of ether
  4. washwashed twice with a saturated aqueous solution of sodium hydrogencarbonate, twice with water
  5. dry with materialtwice with saturated brine and dried over magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThereafter, the purification
  8. distillationwas conducted by distillation under reduced pressure

Sources & evidence

ORD record
ord-e0b2242ef7f0441e94df8cb04b7ab31f
Source dataset
uspto-grants-2011_02
Patent number
US07879960B2

Reaction notes

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