Allyl bromide → HCID 13298915, compound

HRID 359497Notes

Reaction equation

HRID 359497 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7](=[O:13])[CH:6]=[CH:5]2.C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22]>CC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:22][CH:21]=[CH2:20])[O:8][C:7](=[O:13])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 54129132H-1-Benzopyran-2-one, 7-hydroxy-6-methyl-

Product 1

HCID 13298915HCID 13298915, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-methyl-7-hydroxycoumarin (I) (14.5 g), anhydrous K2CO3 (5 g), allyl bromide (15 ml) and acetone (400 ml) was refluxed for 12 h under stirring. From the refluxed mixture the solid was filtered and washed several times with acetone. The acetonic solution and the pooled washings were concentrated to dryness and the residue crystallized from MeOH, yielding 6-methyl-7-allyloxycoumarin (IV) (11.4 g; m.p. 124°-5° C.). ##STR10##

Workup

  1. temperaturewas refluxed for 12 h
  2. filtrationFrom the refluxed mixture the solid was filtered
  3. washwashed several times with acetone
  4. concentrationThe acetonic solution and the pooled washings were concentrated to dryness
  5. customthe residue crystallized from MeOH

Sources & evidence

ORD record
ord-1ad8c1e128114636b8e0cdfb891a0a9c
Source dataset
uspto-grants-1991_03
Patent number
US05001147

Reaction notes

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