Coumarin → 2-Ethenylphenol

HRID 2357426Notes

Reaction equation

HRID 2357426 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5]C(O)=O.O1C2C(=CC=CC=2)C=CC1=O.[Li+].[OH-].N1C=CN=C1>CS(C)=O>[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 323CoumarinHCID 795ImidazoleHCID 3939Lithium HydroxideHCID 119683-(2-Hydroxyphenyl)-2-propenoic acid

Product 1

HCID 1354422-EthenylphenolYield 58%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-hydroxycinnamic acid or coumarin (2H-1-Benzopyran-2-one) (0.0083 mol), LiOH (10%, 4 mL), imidazole (1 mL) and dimethylsulphoxide were taken in a 100 ml round bottom flask fitted with reflux condenser. The flask was placed inside the microwave oven and irradiated (200 W, 180° C.) for 5-8 minutes. After completion of reaction, it was worked up and purified as in example V and provided viscous liquid. 58% yield; 1H NMR (CDCl3) δ 7.40 (1H, d, J=7.67 Hz), 7.14 (1H, m), 6.95 (2H, m), 6.80 (1H, d, J=8.07 Hz), 5.78 (1H, d, J=17.10 Hz), 5.37 (1H, d, J=11.20 Hz), 5.01 (1H, s); 13C NMR (CDCl3) δ 153.1, 132.2, 129.8, 128.4, 125.6, 121.8, 116.7 and 116.4.

Workup

  1. customwere taken in a 100 ml round bottom flask
  2. customfitted
  3. temperaturewith reflux condenser
  4. customirradiated (200 W, 180° C.) for 5-8 minutes
  5. customAfter completion of reaction, it
  6. custompurified as in example V
  7. customprovided viscous liquid

Sources & evidence

ORD record
ord-3971eca49e304bf9b9e9e0fd7b3caa78
Source dataset
uspto-grants-2010_07
Patent number
US07759527B2

Reaction notes

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