Sodium Hydroxide → 3-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acid

HRID 1436625Notes

Reaction equation

HRID 1436625 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[C:7]([C:8]([O:10]CC)=[O:9])[CH:6]=1)[CH3:2].[OH-].[Na+]>CC(C)=O.C(O)C>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 610139Diethyl 5-(hydroxymethyl)isophthalate

Product 1

HCID 210858293-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acidYield 43%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

Add a solution of diethyl-5-(hydroxymethyl)-isophthalate (5 g, 19.8 mmol) in acetone (88 mL) to a solution of NaOH (792 mg, 19.8 mmol) in ethanol (12 mL). After 4 h collect precipitate. Dissolve the precipitate in water (200 mL), add 5 N HCl to about about pH=1 and collect the precipitate. Extract the aqueous with dichloromethane, combine the extracts with the precipitate and concentrate to give to give the title compound (1.9 g, 43%)

Workup

  1. customAfter 4 h collect precipitate
  2. dissolutionDissolve the precipitate in water (200 mL)
  3. additionadd 5 N HCl to about about pH=1
  4. customcollect the precipitate
  5. extractionExtract the aqueous with dichloromethane
  6. concentrationconcentrate
  7. customto give

Sources & evidence

ORD record
ord-d4d9bf554b304a458f721760dcf9a4e1
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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