Allyl bromide → HCID 13298915, compound

HRID 1646419Notes

Reaction equation

HRID 1646419 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.). ##STR9##

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-1c872c27a0b841ddbd7882b0742c0ca1
Source dataset
uspto-grants-1993_01
Patent number
US05179217

Reaction notes

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