Acetic Anhydride → HCID 13298921, compound

HRID 359499Notes

Reaction equation

HRID 359499 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:13][CH:14]=[CH2:15])[C:11]=1[OH:12])[O:8][C:7](=[O:16])[CH:6]=[CH:5]2.[C:17](O[Na])([CH3:19])=[O:18].C(OC(=O)C)(=O)C>O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:13][CH:14]=[CH2:15])[C:11]=1[O:12][C:17](=[O:18])[CH3:19])[O:8][C:7](=[O:16])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 13298918HCID 13298918, compoundHCID 178418247HCID 178418247, compound

Product 1

HCID 13298921HCID 13298921, compoundYield 129.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In such a manner a mixture of 6-methyl-7-hydroxy-8-allylcoumarin (VII) (6.3 g), anhydrous AcONa (1.5 g) and acetic anhydride (40 ml) was refluxed for 1 h. The reaction mixture was gently diluted with water (40 ml), refluxed for 10 min and then poured into H2O (300 ml) yielding a precipitate, which was collected by filtration and washed several times with H2O. The dried product was crystallized from MeOH yielding 6-methyl-7-acetoxy-8-allylcoumarin (X) (6.1 g; m.p. 110°-11° C.). ##STR16##

Workup

  1. temperaturewas refluxed for 1 h
  2. temperaturerefluxed for 10 min
  3. customyielding a precipitate, which
  4. filtrationwas collected by filtration
  5. washwashed several times with H2O
  6. customThe dried product was crystallized from MeOH

Sources & evidence

ORD record
ord-348a72d80e5d46ebbc20f8ce8d4861c0
Source dataset
uspto-grants-1991_03
Patent number
US05001147

Reaction notes

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