Acetic Acid → HCID 86662536, compound

HRID 1957809Notes

Reaction equation

HRID 1957809 reaction equation
[C:1]([C:5]1[CH2:9][CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:10](O)(=O)[CH3:11]>CC(C)=O>[C:1]([C:5]1[CH:9]=[C:8]2[C:7](=[C:10]([CH3:11])[CH2:2][C:1]2([CH3:4])[CH3:3])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 633714Tert-butylcyclopentadiene

Product 1

HCID 86662536HCID 86662536, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 1000 ml five neck flask, 24.97 g (204 mmol) of tert-butylcyclopentadiene and 399.04 g of acetone were placed. In an ice water bath, 82.1 g (1.15 mol) of pyrolydine was dropwise added, followed by stirring for 18 hours under reflux. In an ice water bath, 70.91 g (1.18 mol) of acetic acid was dropwise added. From the resulting crude product, the solvent was distilled off under reduced pressure (150 torr, 40° C.), and the resulting product was washed with water, a 5% acetic acid solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated saline solution, followed by drying over magnesium sulfate. After the solvent was distilled off, the remainder was purified by vacuum distillation, whereby 23.4 g of 5-tert-butyl-1,1,3-trimethyl-1,2-dihydropentalene represented by the following formula [1] was obtained. Identification was carried out by a 1H-NMR spectrum and a GC-mass spectrometry spectrum (GC-MS). The results of the measurement are given below.

Workup

  1. additionIn an ice water bath, 82.1 g (1.15 mol) of pyrolydine was dropwise added
  2. temperatureunder reflux
  3. distillationFrom the resulting crude product, the solvent was distilled off under reduced pressure (150 torr, 40° C.)
  4. washthe resulting product was washed with water
  5. dry with materialby drying over magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. distillationthe remainder was purified by vacuum distillation, whereby 23.4 g of 5-tert-butyl-1,1,3-trimethyl-1,2-dihydropentalene
  8. customwas obtained
  9. customThe results of the measurement

Sources & evidence

ORD record
ord-2d9c972faa7a4c6a99be7accac8a28c4
Source dataset
uspto-grants-2013_04
Patent number
US08409480B2

Reaction notes

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