6-Allyl-7-hydroxy-8-methoxycoumarin → 7-Acetoxy-6-allyl-8-methoxycoumarin

HRID 66072

Reaction equation

HRID 66072 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([O:15][CH3:16])[C:13]=1[OH:14])[O:10][C:9](=[O:17])[CH:8]=[CH:7]2)[CH:2]=[CH2:3].[C:18](OC(=O)C)(=[O:20])[CH3:19].N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:18]([O:14][C:13]1[C:12]([O:15][CH3:16])=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:17])[O:10]2)=[CH:5][C:4]=1[CH2:1][CH:2]=[CH2:3])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 218145006-Allyl-7-hydroxy-8-methoxycoumarinHCID 22348678Acetic anhydride pyridine

Product 1

HCID 218145017-Acetoxy-6-allyl-8-methoxycoumarin

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2.32g. (0.010 mole) of 6-allyl-7-hydroxy-8-methoxycoumarin in 8 ml. of chloroform was treated with 4.5 ml. of acetic anhydride/pyridine, 1:2. The reactants were stirred at 25° for 2.0 hours and then partitioned between 1N HCl/methylene chloride. The aqueous phase was further extracted with methylene chloride. The organic extracts were combined, dried over sodium sulfate, and evaporated to afford pure 7-acetoxy-6-allyl-8-methoxycoumarin as a white solid, mp 101°-102°. Recrystallization from ethanol afforded an analytical sample, mp 102°-103°.

Workup

  1. custompartitioned between 1N HCl/methylene chloride
  2. extractionThe aqueous phase was further extracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-35cc6a46e79b46c6b636d3fe1c0ddc5b
Source dataset
uspto-grants-1978_12
Patent number
US04130568

Linked notes

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