Tetrahydrofuran → 2,6-Di-tert-butyl-4-[(2-methylcyclopenta-1,3-dien-1-yl)methyl]phenol

HRID 1980008Notes

Reaction equation

[CH3:1][C:2]1[CH2:6][CH:5]=[CH:4][CH:3]=1.[C:7]([C:11]1[CH:16]=[C:15](N(C)C)[CH:14]=[C:13]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:12]=1[OH:24])([CH3:10])([CH3:9])[CH3:8].O1CCC[CH2:26]1.[Na]>O>[CH3:1][C:2]1[CH:6]=[CH:5][CH2:4][C:3]=1[CH2:26][C:15]1[CH:16]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:12]([OH:24])=[C:13]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred mixture of 40 g (0.5 m) methylcyclopentadiene, 39.5 g (0.15 m) 2,6-di-t-butyl-4-dimethylaminophenol and 100 ml of tetrahydrofuran was slowly added 6.0 g (0.26 m) of sodium. The temperature was raised to 70° C. and the mixture allowed to react for 20 hours. A gas chromatograph showed that all of the 2,6-di-t-butyl-4-dimethylaminophenol had reacted. The mixture was diluted with water, extracted with toluene and rotovaped to remove the toluene and leave 38 g of crude product. A 90% yield, 31.5 g, of pure product methyl-(3,5-di-tert-butyl-4-hydroxybenzyl)cyclopentadiene was obtained by distillation, b.p. 155° to 160° C. at 1.5 mm as a viscous yellow oil. After standing at room temperature for 2 weeks, the material was analyzed by mass spectral analysis and by gas chromatography. Both showed that the product and its dimer were present. The mass spectrum showed a 3 to 1 ratio of the monomer to dimer, m/e 298 and m/e 596, respectively. The gas chromatograph showed a sharp peak for the monomer followed by the broad peak due to the slow decomposition of the dimer.

Workup

customto react for 20 hours
customhad reacted
extractionextracted with toluene
customto remove the toluene
customleave 38 g of crude product

Sources & evidence

ORD record: ord-8ced1c6af419476180317c692fb3b1f0
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04484010

Reaction notes

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