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

HRID 511902Notes

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.CC(C1C=CC=CC=1)=C>[C].[Pd]>[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

Conditions

Temperature: 150 °C

Procedure

After the water layer was separated, the oil layer was condensed or otherwise adjusted so that the concentration of the mixture of 1,3-bis(4-hydroxyphenyl)-1-cyclohexene and 1,5-bis(4-hydroxyphenyl)-1-cyclohexene became 17%. 79.6 g of the concentration-adjusted solution, 14.8 g of α-methyl styrene and 0.8 g of 5% palladium carbon were introduced to an autoclave and agitated for 6 hours at 150° C. After the reaction, the reaction liquid was filtered to remove the 5% palladium carbon, and then the methyl isobutyl ketone was distilled out, after which 40 g of toluene was added and the separated crystal was filtered out and dried to obtain 6.9 g of 4,4″-dihydroxy-m-terphenyl of 97% purity (high-speed liquid chromatography) [Step (C)].

Workup

customAfter the water layer was separated
customcondensed
customAfter the reaction
customthe reaction liquid
filtrationwas filtered
customto remove the 5% palladium carbon
distillationthe methyl isobutyl ketone was distilled out
additionafter which 40 g of toluene was added
filtrationthe separated crystal was filtered out
customdried

Sources & evidence

ORD record: ord-e74fbb7c34e14878b4acfee40fb84a82
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102596B2

Reaction notes

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