Alpha-Methylstyrene → HCID 117964206, compound

HRID 511903Notes

Reaction equation

HRID 511903 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH3:9])=[CH:4][C:3]=1[C:10]1[CH2:15][CH:14]([C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[CH:18][C:17]=2[CH3:24])[CH2:13][CH2:12][CH:11]=1.CC(C1C=CC=CC=1)=C>C(C(C)=O)C(C)C.[C].[Pd]>[CH3:24][C:17]1[CH:18]=[C:19]([OH:23])[C:20]([CH3:22])=[CH:21][C:16]=1[C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([C:3]2[CH:4]=[C:5]([CH3:9])[C:6]([OH:8])=[CH:7][C:2]=2[CH3:1])[CH:15]=1

Participants

5

Reactant 2

HCID 7407Alpha-MethylstyreneHCID 117964252HCID 117964252, compound

Product 1

HCID 117964206HCID 117964206, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 7909Methyl Isobutyl KetoneSolvent2×

Conditions

Temperature
150 °C

Procedure

3.0 g of the 98.7% pure 1,5-bis(2,5-dimethyl-4-hydroxyphenyl)-1-cyclohexene obtained in Step (D) of Example 5, 30 g of methyl isobutyl ketone, 3.0 g of α-methyl styrene, and 0.63 g of 5% palladium carbon were introduced to an autoclave and then heated to 150° C. to be reacted for 46.5 hours at the same temperature under agitation. After heating, 0.63 g of 5% palladium carbon was added after 18 hours and again after 34 hours, respectively. The mixture was heated further to 190° C. and agitated for 6 hours at the same temperature to cause reaction, after which the palladium carbon was filtered out and the obtained filtrate was condensed. The obtained residue was dissolved in methyl isobutyl ketone to separate the crystal, which was then filtered out and dried to obtain 1.4 g of 2,2″,5,5″-tetramethyl-4,4″-dihydroxy-m-terphenyl of 94.5% purity (according to high-speed liquid chromatography).

Workup

  1. customto be reacted for 46.5 hours at the same temperature under agitation
  2. temperatureAfter heating
  3. temperatureThe mixture was heated further to 190° C.
  4. customreaction
  5. filtrationafter which the palladium carbon was filtered out
  6. customcondensed
  7. customto separate the crystal, which
  8. filtrationwas then filtered out
  9. customdried

Sources & evidence

ORD record
ord-27c7dcd9f43d42908ae68d8a18e2f6af
Source dataset
uspto-grants-2015_08
Patent number
US09102596B2

Reaction notes

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