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

HRID 1181940Notes

Reaction equation

HRID 1181940 reaction equation
[Br:1][C:2]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:3]=1[O:4]/[C:5](=[CH:11]\[C:12]([O:14]CC)=[O:13])/[C:6]([O:8]CC)=[O:7].[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:3]=1[O:4]/[C:5](=[CH:11]\[C:12]([OH:14])=[O:13])/[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86587184diethyl (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-a4fd7da384624437881122380ff4e519
Source dataset
uspto-grants-2007_10
Patent number
US07285662B2

Reaction notes

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