Dabco → 5-Methoxy-1,3-dihydro-2-benzofuran-1,3-dione

HRID 1966720Notes

Reaction equation

HRID 1966720 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=O.S(Cl)(Cl)=O.C1N2CCN(CC2)C1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:10][CH:11]=1)[C:7](=[O:9])[O:14][C:12]2=[O:13]

Participants

5

Reactant 3

HCID 9237DabcoHCID 24386Thionyl ChlorideHCID 746654-Methoxyphthalic acid

Product 1

HCID 6397485-Methoxy-1,3-dihydro-2-benzofuran-1,3-dioneYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-methoxy-phthalic acid (1.8 g, 9.18 mmol), thionyl chloride (1.4 mL, 19.79 mmol) in CH2Cl2 (15 mL) is added DABCO (1.1 g, 9.81 mmol). The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with CH2Cl2 (100 mL), washed with H2O (75 mL×2), dried with Na2SO4 and filtered. The filtrate is concentrated under reduced pressure to afford 5-methoxy-isobenzofuran-1,3-dione (950 mg, 58%).

Workup

  1. washwashed with H2O (75 mL×2)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-5d5d18daad334ca084c60a0f35f02b5b
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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