Potassium Hydroxide → HCID 22616362, compound

HRID 842958Notes

Reaction equation

HRID 842958 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[C:6]([C:13]2[CH:14]=[C:15]([C:24]([O:26]CC)=[O:25])[C:16](=[CH:22][CH:23]=2)[C:17]([O:19]CC)=[O:18])=[CH:5][CH:4]=1.BrC1C=C(C(OCC)=O)C(=CC=1)C(OCC)=O.[OH-].[K+]>C(O)C>[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[C:6]([C:13]2[CH:14]=[C:15]([C:24]([OH:26])=[O:25])[C:16](=[CH:22][CH:23]=2)[C:17]([OH:19])=[O:18])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 181582Benzene-1,2-dicarboxylic acid, 4-bromo-, diethyl esterHCID 22616365HCID 22616365, compound

Product 1

HCID 22616362HCID 22616362, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of diethyl 4-(8-methoxy-1,4-benzodioxan-5-yl)phthalate (0.69 g, 1.8 mmol) obtained by treating Compound A (0.70 g, 3.3 mmol) obtained in Reference Example 1 and known diethyl 4-bromophthalate (1.00 g, 3.3 mmol) by the same reaction as in Example 17 were added ethanol (7.0 mL) and a 6 mol/L aqueous solution of potassium hydroxide (1.4 mL), the mixture was stirred at room temperature for 2 hours, and then ethanol was evaporated in vacuo. Water was added to the resulting solution, the mixture was adjusted to pH 2 with 6 mol/L hydrochloric acid, and the precipitated solid was collected by filtration and dried in vacuo to give Compound B (0.55 g, 94%) as a white solid.

Workup

  1. customobtained
  2. customobtained in Reference Example 1
  3. customby the same reaction as in Example 17
  4. customethanol was evaporated in vacuo
  5. additionWater was added to the resulting solution
  6. filtrationthe precipitated solid was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b0ba042c9b144eca8e3dc7a5584fb9b8
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

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