Dimethyl Sulfoxide → 2-(p-Biphenylyl)-3-butyn-2-ol

HRID 437923

Reaction equation

[C:1]1([C:7]2[CH:12]=[CH:11][C:10](C(=O)C)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(C)=O.[OH2:20]>>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=1[C:2]([OH:20])([C:1]#[CH:6])[CH3:3]

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 962Water

HCID 71134-Acetylbiphenyl

Product 1

HCID 867348962-(p-Biphenylyl)-3-butyn-2-ol

Procedure

To a solution of 46.6 g of p-phenylacetophenone in 250 ml. of dimethyl sulfoxide, there is added 65.5 g of lithium acetylide - ethylene diamine complex. After 18 hours at room temperature, the mixture is poured on 2 liters of iced water. The initial oil solidifies on standing, is filtered off and recrystallized from 150 ml of isopropyl alcohol to give 2-(p-biphenylyl)-3-butyn-2-ol, mp 75°-80° C.

Workup

filtrationThe initial oil solidifies on standing, is filtered off
customrecrystallized from 150 ml of isopropyl alcohol

Sources & evidence

ORD record: ord-efd70c0ac46345d78a20218445e27eac
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04032580

Linked notes

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