N,N-Diethylaniline → 8-allyl-7-hydroxy-4-methyl-chromen-2-one

HRID 848153Notes

Reaction equation

HRID 848153 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH3:16])=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)C=C.C(N(CC)[C:20]1[CH:25]=CC=C[CH:21]=1)C>>[CH2:25]([C:14]1[C:5]([OH:4])=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11](=[O:15])[CH:10]=[C:9]2[CH3:16])[CH:20]=[CH2:21]

Participants

3

Reactant 2

HCID 7061N,N-DiethylanilineHCID 2389527-(Allyloxy)-4-methyl-2H-chromen-2-one

Product 1

HCID 57131038-allyl-7-hydroxy-4-methyl-chromen-2-oneYield 65%

Procedure

Crude 7-allyloxy-4-methylcoumarin (83.5 g, 0.381 mol) was dissolved in 250 ml of diethyl aniline with heating, and the solution was allowed to reflux for two hours. After the solution had cooled and some product had precipitated, petroleum ether (b.p. 30°-60° C., 760 ml) was added. A brown precipitate formed and was collected by filtration, washed with three small portions of petroleum ether, and dried in vacuo to obtain the crude product. Recrystallization from 600 ml of 95% EtOH gave the pure product (53.5 g, 74% recovery, 65% yield) of mp 192.5°-195.0° C. (lit. 193°-194° C.). TLC showed only a single spot.

Workup

  1. temperaturewith heating
  2. temperatureto reflux for two hours
  3. temperatureAfter the solution had cooled
  4. customsome product had precipitated
  5. additionpetroleum ether (b.p. 30°-60° C., 760 ml) was added
  6. customA brown precipitate formed
  7. filtrationwas collected by filtration
  8. washwashed with three small portions of petroleum ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-121167d53c244955836c4dd8d04576b3
Source dataset
uspto-grants-1981_10
Patent number
US04294847

Reaction notes

Loading…