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

HRID 1436661Notes

Reaction equation

HRID 1436661 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+]>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

4

Reactant 2

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

Product 1

HCID 210858293-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acidYield 74.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add commercially available 5-hydroxymethyl-isophthalic acid diethyl ester (5 g, 19.8 mmol) and NaOH (0.79 g, 19.8 mmol) to ethanol (100 mL). Stir for 4 h at room temperature. Concentrate and pour the residue into water (100 mL) and diethyl ether (100 mL). Separate the aqueous layer and wash it with diethyl ether (40 mL). Acidify the aqueous layer with 5 N HCl to about pH=1. Extract the acidic solution with ethyl acetate (3×40 mL). Wash the combined organic layers with Water, saturated aqueous sodium chloride, dry (sodium sulfate) and concentrate to give the title compound as a solid (3.3 g, 74%).

Workup

  1. concentrationConcentrate
  2. additionpour the residue into water (100 mL) and diethyl ether (100 mL)
  3. customSeparate the aqueous layer
  4. washwash it with diethyl ether (40 mL)
  5. extractionExtract the acidic solution with ethyl acetate (3×40 mL)
  6. washWash the combined organic layers with Water, saturated aqueous sodium chloride
  7. dry with materialdry (sodium sulfate)
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-ff591be856664e88b2a9b7b4ecd2ac4c
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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