Sodium Hydroxide → (2Z)-2-(2-bromo-4-methoxyphenoxy)-2-butenedioic acid

HRID 2414481Notes

Reaction equation

HRID 2414481 reaction equation
[Br:1][C:2]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:3]=1[O:4]/[C:5](=[CH:9]\[C:10]([O-:12])=[O:11])/[C:6]([O-:8])=[O:7].[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:3]=1[O:4]/[C:5](=[CH:9]\[C:10]([OH:12])=[O:11])/[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86759554(2Z)-2-(2-bromo-4-methoxyphenoxy)-2-butenedioate

Product 1

HCID 69270394(2Z)-2-(2-bromo-4-methoxyphenoxy)-2-butenedioic acidYield 88.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Diethyl, (2Z)-2-(2-bromo-4-methoxyphenoxy)-2-butenedioate (29.9 g, 86.6 mmol) as prepared in Reference Example 2a was suspended in ethanol (55 ml) and a solution of sodium hydroxide (7.0 g, 0.175 mol) in water (55 ml) was added. The solution was refluxed for 1 h to give a clear orange solution. Most of the ethanol was removed in vacuo then 6 M HCl (50 ml) was added. The solid was filtered, washed with water and dried to give (2Z)-2-(2-bromo-4-methoxyphenoxy)-2-butenedioic acid as a light orange solid (24.3 g, 88% yield).

Workup

  1. temperatureThe solution was refluxed for 1 h
  2. customto give a clear orange solution
  3. customMost of the ethanol was removed in vacuo
  4. addition6 M HCl (50 ml) was added
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-6b3f473a634d4ace97ed17843238e244
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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