HCID 54462223, compound → HCID 9948069, compound

HRID 344925Notes

Reaction equation

C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][C:6]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19]CC=C)=[CH:15][CH:14]=1)C=C>C1C2C(=CC=CC=2)CCC1>[CH2:10]([C:10]1[CH:9]=[C:8]([CH2:11][CH3:12])[CH:7]=[C:6]([C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[C:17]([CH2:9][CH:8]=[CH2:7])[CH:18]=2)[C:5]=1[OH:4])[CH:5]=[CH2:6]

Participants

Conditions

Temperature: 200 °C

Procedure

A solution was prepared by dissolving 58.4 g of 2,4'-diallyloxy-5-ethylbiphenyl into 200 ml of tetrahydronaphthalene. The solution was heated at 200° C. with nitrogen gas blowing for 8 hours with stirring, cooled, extracted with 10% sodium hydroxide and washed with n-hexane. The extract, which was acidified with hydrochloric acid, was extracted with diethylether. The extract was washed with an aqueous solution saturated with NaCl, and 10% water solution of sodium hydrogencarbonate, dried with sodium sulfate and concentrated. The concentrate was purified by a silica gel column-chromatography (n-hexane:ethylacetate=15:1) and recrystallized from n-hexane to yield white powder 40 g of 3,3'-diallyl-5-ethyl-2,4'-biphenyldiol having a m.p. of 47°-48° C.

Workup

customA solution was prepared
temperaturecooled
extractionextracted with 10% sodium hydroxide
washwashed with n-hexane
extractionwas extracted with diethylether
washThe extract was washed with an aqueous solution saturated with NaCl, and 10% water solution of sodium hydrogencarbonate
dry with materialdried with sodium sulfate
concentrationconcentrated
customThe concentrate was purified by a silica gel column-chromatography (n-hexane:ethylacetate=15:1)
customrecrystallized from n-hexane

Sources & evidence

ORD record: ord-dd37fcc77f454f709743456c6b001c38
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053548

Reaction notes

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