Water → 4-(Prop-2-YN-1-YL)benzoic acid

HRID 271599Notes

Reaction equation

HRID 271599 reaction equation
[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)[C:2]#[CH:3].O.Cl([O-])=[O:14].[Na+]>C1COCC1>[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([OH:14])=[O:9])=[CH:10][CH:11]=1)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 962Water2×HCID 136813684-(Prop-2-YN-1-YL)benzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 227233984-(Prop-2-YN-1-YL)benzoic acidYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-prop-2-ynyl-benzaldehyde (10 mmol) in THF (30 ml), amidosurfulic acid (16 mmol) and water (15 ml) solution of sodium chlorite (30 mmol) are added. The reaction mixture is stirred at room temperature for 2 h. Water is added and then aqueous layer is extracted with two 50 ml portions of CH2Cl2. The combined extracts are washed with brine, dried over sodium sulfate and concentrated under vacuum to give crude product which is purified by silica gel column chromatography. Yield: 62%. Rf=0.44 (n-hexane:AcOEt=7:3)

Workup

  1. extractionaqueous layer is extracted with two 50 ml portions of CH2Cl2
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give crude product which
  6. customis purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fa829f32ecb04aebbbb837fd70ecaff9
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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