Alpha-Methylstyrene → [1,1';3',1'']Terphenyl-4,4''-diol

HRID 511901Notes

Reaction equation

HRID 511901 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH:9]=2)=[CH:4][CH:3]=1.OC1C=CC(C2CC(C3C=CC(O)=CC=3)CCC=2)=CC=1.C(C(C)=O)C(C)C.CC(C1C=CC=CC=1)=C>C(OCC)(=O)C.[C].[Pd].C1CCCCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 7407Alpha-MethylstyreneHCID 7909Methyl Isobutyl KetoneHCID 117964207HCID 117964207, compoundHCID 117964259HCID 117964259, compound

Product 1

HCID 667696[1,1';3',1'']Terphenyl-4,4''-diolYield 33%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

2.6 g of the 91% pure mixture of 1,3-bis(4-hydroxyphenyl)-1-cyclohexene and 1,5-bis(4-hydroxyphenyl)-1-cyclohexene obtained in Step (B), 15.6 g of methyl isobutyl ketone, 3.5 g of α-methyl styrene, and 0.2 g of 5% palladium carbon were introduced to an autoclave and agitated for 6 hours at 150° C. After the end of reaction, the reaction liquid was filtered to remove the 5% palladium carbon, and then the filtrate was condensed. The residue was dissolved in 3.2 g of ethyl acetate, after which 7.5 g of cyclohexane was added to the mixture and the separated crystal was filtered out and dried to obtain 1.9 g of 4,4″-dihydroxy-m-terphenyl of 99% purity (high-speed liquid chromatography).

Workup

  1. customAfter the end of reaction
  2. customthe reaction liquid
  3. filtrationwas filtered
  4. customto remove the 5% palladium carbon
  5. customcondensed
  6. filtrationthe separated crystal was filtered out
  7. customdried

Sources & evidence

ORD record
ord-649842d47d5c4fa09579768c45333878
Source dataset
uspto-grants-2015_08
Patent number
US09102596B2

Reaction notes

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