Hydrochloric Acid → 7-Hydroxy-4-methoxymethyl-8-methylcoumarin

HRID 1281648Notes

Reaction equation

HRID 1281648 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:14])[C:9]([OH:13])=[CH:10][CH:11]=2)[O:6][C:5](=[O:15])[CH:4]=1.[CH3:16][O-:17].[Na+].Cl>CO.C(O)(C)C>[OH:13][C:9]1[C:8]([CH3:14])=[C:7]2[C:12]([C:3]([CH2:2][O:17][CH3:16])=[CH:4][C:5](=[O:15])[O:6]2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 54238774-(chloromethyl)-7-hydroxy-8-methyl-2H-chromen-2-oneHCID 10942334Sodium Methoxide

Product 1

HCID 184214487-Hydroxy-4-methoxymethyl-8-methylcoumarin

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloromethyl-7-hydroxy-8-methylcoumarin (2.00 g, 8.90 mmol) and sodium methoxide (12.0 g, 222 mmol) in methanol (400 mL) was refluxed overnight. The solution was allowed to cool to room temperature, acidified to pH 0-1 with 5-6N HCl in isopropanol and evaporated. The residue was azeotroped with toluene several times to give crude product 7-hydroxy-4-methoxymethyl-8-methylcoumarin, a yellow oil. 1H NMR (CD3OD): δ7.38 (d, J=8.5 Hz, 1H), 6.82 (d, J=8.8 Hz, 1H), 6.29 (s, 1H), 4.66 (s, 2H), 3.51 (s, 3H), 2.26 (s, 3H).

Workup

  1. temperaturewas refluxed overnight
  2. customevaporated
  3. customThe residue was azeotroped with toluene several times

Sources & evidence

ORD record
ord-40417ee35581422b9c2f30d91a1e9b3e
Source dataset
uspto-grants-2002_09
Patent number
US06455286B1

Reaction notes

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