Octane → HCID 86748707, compound

HRID 2257355Notes

Reaction equation

HRID 2257355 reaction equation
[F:1][C:2]1[C:3]([OH:12])=[C:4]([C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)[CH:5]=O.[C:13](#[N:16])[CH:14]=[CH2:15].CCCCCCCC>>[C:13]([C:14]1[CH2:15][O:12][C:3]2[C:4]([CH:5]=1)=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:2]=2[F:1])#[N:16]

Participants

4

Reactant 3

HCID 356OctaneHCID 7855AcrylonitrileHCID 190282303-Fluoro-2-hydroxy-6-methoxybenzaldehyde

Product 1

HCID 86748707HCID 86748707, compoundYield 13.6%

Procedure

Crude 3-fluoro-hydroxy-6-methoxybenzaldehyde (8.0 g) from above, acrylonitrile (13 mL; 193 mmol) and 1,4.diazadicyclo [2,2,2] octane (0.66 g; 5.9 mmol) were refluxed in a three-necked round-bottom flask (50 mL) under nitrogen for 4 h. Rotary-evaporation of the volatiles left a thick, red oil which was flash-chromatographed on a silica column eluted with methylene chloride/n-hexane (4:5). Concentration of relevant fractions gave an impure product (91% GC) which was crystallized form EtOAc to give 1.31 g of the title compound as colourless bars. Mp. 133°-135° C.

Workup

  1. customRotary-evaporation of the volatiles
  2. waitleft a thick, red oil which
  3. customwas flash-chromatographed on a silica column
  4. washeluted with methylene chloride/n-hexane (4:5)
  5. customConcentration of relevant fractions gave an impure product (91% GC) which
  6. customwas crystallized form EtOAc

Sources & evidence

ORD record
ord-3825d990f84d421aa70fe00cdb757486
Source dataset
uspto-grants-1997_08
Patent number
US05656658

Reaction notes

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