Water → 3-Prop-1-ynyl-1-benzofuran-5-carboxylic acid

HRID 2181687Notes

Reaction equation

HRID 2181687 reaction equation
[C:1]([C:4]1[C:8]2[CH:9]=[C:10]([C:13]([O:15]C)=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][CH:5]=1)#[C:2][CH3:3].[OH-].[Na+].O>CO>[C:1]([C:4]1[C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][CH:5]=1)#[C:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22481806Methyl 3-prop-1-ynyl-1-benzofuran-5-carboxylate

Product 1

HCID 693618473-Prop-1-ynyl-1-benzofuran-5-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-prop-1-ynyl-1-benzofuran-5-carboxylate (388 mg, 1.81 mmol) is dissolved in 10 ml MeOH. The solution is treated with 2N NaOH (2.3 ml, 4.6 mmol) followed by 2 ml H2O and the reaction is stirred overnight at RT. The reaction is concentrated to dryness, the residue is dissolved in 9 ml H2O, and the pH is adjusted to 3 with 10% aqueous HCl. The precipitate is collected, washed with H2O, and is dried to afford 356 mg (98%) of 3-prop-1-ynyl-1-benzofuran-5-carboxylic acid as an off-white solid. HRMS (EI) calcd for C12H8O3: 200.0473, found 200.0476 (M+).

Workup

  1. concentrationThe reaction is concentrated to dryness
  2. dissolutionthe residue is dissolved in 9 ml H2O
  3. customThe precipitate is collected
  4. washwashed with H2O
  5. customis dried

Sources & evidence

ORD record
ord-6dd6aafa428f4ce29f4765f28bef85c0
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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