Coumarin → HCID 2300725, compound

HRID 2413982Notes

Reaction equation

HRID 2413982 reaction equation
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]1=[O:3].[OH-:12].[K+].[CH2:14](Br)[CH:15]=[CH2:16]>CS(C)=O>[CH2:14]([O:1][C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:5]=[CH:4]\[C:2]([OH:3])=[O:12])[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 323CoumarinHCID 7841Allyl bromideHCID 14797Potassium Hydroxide

Product 1

HCID 2300725HCID 2300725, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A slurry of coumarin (14.6 g, 0.10 mol) and potassium hydroxide (83 g, 1.48 mol) in 300 mL dimethyl sulfoxide was stirred at ambient temperature for 4 hours. Allyl bromide (8.66 mL, 0.10 mol) was added over 5 minutes and the reaction stirred at ambient temperature for 30 minutes. The mixture was poured into ice water, the solution filtered and then acidified (pH<3.0) with hydrochloric acid. The solid was filtered, air dried, then recrystallized from methlcyclohexane to yield cream needles (12.04 g, 59.0%), mp 80°-82° C.

Workup

  1. filtrationthe solution filtered
  2. filtrationThe solid was filtered
  3. customair dried
  4. customrecrystallized from methlcyclohexane

Sources & evidence

ORD record
ord-62dddf52e66d4e8c8d4863705078307b
Source dataset
uspto-grants-1988_01
Patent number
US04720559

Reaction notes

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