Dimethyl 2-methoxybenzene-1,3-dicarboxylate → dimethyl 2-hydroxyisophthalate

HRID 2393718Notes

Reaction equation

HRID 2393718 reaction equation
C[O:2][C:3]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>C(Cl)Cl>[OH:2][C:3]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

3

Reactant 1

HCID 15708503Dimethyl 2-methoxybenzene-1,3-dicarboxylate

Product 1

HCID 10889156dimethyl 2-hydroxyisophthalate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethyl 2-methoxyisophthalate, prepared according to Example 4, (279 mg, 1.24 mmol) was dissolved in dry CH2Cl2 (5 ml), and the flask was flushed with argon. Boron trichloride (1M solution in heptane, 1.2 ml) was added, and the solution was stirred under argon for 1 hour at room temperature. After evaporation of the solvent, chromatography with 3:7 EtOAc:petroleum ether gave the product as a white solid. Yield: 237 mg (91%). 1H NMR (CDCl3) δ: 8.06 (d, 2 H, aryl), 6.94 (t, 1 H, aryl), 3.96 (s, 6 H, CO2CH3)

Workup

  1. customthe flask was flushed with argon
  2. additionBoron trichloride (1M solution in heptane, 1.2 ml) was added
  3. customAfter evaporation of the solvent, chromatography with 3:7 EtOAc

Sources & evidence

ORD record
ord-c9c8bbcc92d24f1d990acfc5409d0ceb
Source dataset
uspto-grants-1998_09
Patent number
US05808035

Reaction notes

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