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

HRID 368792Notes

Reaction equation

HRID 368792 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): δ 7.38 (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-9ce182e687094fd589fdb936d1fab731
Source dataset
uspto-grants-2000_10
Patent number
US06133460

Reaction notes

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