1,5-Hexadiyne → Nona-2,4,8-triyn-1-ol

HRID 1973997Notes

Reaction equation

HRID 1973997 reaction equation
Br[CH2:2][C:3]#[C:4][OH:5].[CH:6]#[C:7][CH2:8][CH2:9][C:10]#[CH:11]>>[CH2:4]([OH:5])[C:3]#[C:2][C:6]#[C:7][CH2:8][CH2:9][C:10]#[CH:11].[CH2:4]([OH:5])[C:3]#[C:2][C:6]#[C:7][CH2:8][CH2:9][C:10]#[C:11][C:2]#[C:3][CH2:4][OH:5]

Participants

4

Reactant 2

HCID 694021,5-HexadiyneHCID 121808481-Propyn-1-ol, 3-bromo-

Product 2

HCID 21488150Nona-2,4,8-triyn-1-olHCID 54150199Dodeca-2,4,8,10-tetrayne-1,12-diol

Procedure

Employing a Cadiot-Chodkiewicz-type reaction, 3-bromopropyne-1-ol was reacted with 1,5-hexadiyne to give two products, 2,4,8-nonatriyne-1-ol (I) and 2,4,8,10-dodecatetrayne-1,12-diol (II), which were separated by use of appropriate solvents. Oxidative coupling of (I) gave 2,4,8,10,14,16-octadecahexayne-1,18-diol (III).

Sources & evidence

ORD record
ord-68ab5d91dfe149759697a89770a38e2d
Source dataset
uspto-grants-1976_12
Patent number
US03999946

Reaction notes

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