Water → 8-Methylcoumarin

HRID 1099362Notes

Reaction equation

HRID 1099362 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O-])(=[O:13])[CH3:12].[Na+].C(OC(=O)C)(=O)C.O>CCCCCC>[CH3:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:3]2[C:2]=1[O:1][C:11](=[O:13])[CH:12]=[CH:4]2

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 5227773-Methylsalicylaldehyde

Product 1

HCID 157348-MethylcoumarinYield 85%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
177.5 °C

Procedure

The suspension of 2-Hydroxy-3-methyl benzaldehyde (30 gm, 0.220 mole) and anhydrous Sodium acetate (45 gm, 0.55 mole) in Acetic anhydride (45 gm, 0.44 mole) was heated at 175-180° C. for 6 hours. The reaction mixture was cooled; water (150 ml) and Hexane (60 ml) were added. It was stirred for an hour and filtered. The obtained solid was stirred with Diethyl ether (30 ml). Finally the suspension was filtered and dried to give 19 gm desired product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. stirringThe obtained solid was stirred with Diethyl ether (30 ml)
  4. filtrationFinally the suspension was filtered
  5. customdried

Sources & evidence

ORD record
ord-d2f367b4660d452b9b4537e0f3e82b7a
Source dataset
uspto-grants-2012_03
Patent number
US08143424B2

Reaction notes

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