Methanol → HCID 58542053, compound

HRID 1966721Notes

Reaction equation

HRID 1966721 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][C:6]2=[O:13].[CH3:14][O-:15].[Na+].CO>>[CH3:14][O:15][C:6](=[O:13])[C:5]1[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:8]([OH:7])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 6397485-Methoxy-1,3-dihydro-2-benzofuran-1,3-dioneHCID 10942334Sodium Methoxide

Product 1

HCID 58542053HCID 58542053, compound

Procedure

To a mixture of 5-methoxy-isobenzofuran-1,3-dione (950 mg, 5.33 mmol) is added 0.5 M NaOMe in MeOH (16 mL, 18 mmol). The reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is concentrated under reduced pressure and the resulting residue subsequently quenched with 1M HCl aq (100 mL). The quenched reaction mixture is extracted with EtOAc (100 mL×2) and the combined organic layers are dried with Na2SO4 and filtered. The filtrate is concentrated under reduced to afford crude 4-methoxy-phthalic acid 2-methyl ester (850 mg).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe resulting residue subsequently quenched with 1M HCl aq (100 mL)
  3. customThe quenched reaction mixture
  4. extractionis extracted with EtOAc (100 mL×2)
  5. dry with materialthe combined organic layers are dried with Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-1b462c78794b40cbbfb848a519a6fbf8
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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