Methanol → 6-Cyanobenzo[b]thiophene-2-carboxylic acid

HRID 1845125Notes

Reaction equation

HRID 1845125 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]([O:13]C)=[O:12])[S:8][C:7]=2[CH:15]=1)#[N:2].CO.[OH-].[Na+]>O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[S:8][C:7]=2[CH:15]=1)#[N:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11031280Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

Product 1

HCID 106796506-Cyanobenzo[b]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round bottom flask was charged with methyl 6-cyanobenzo[b]thiophene-2-carboxylate (4.00 g, 17.9 mmol), methanol (130 mL), and sodium hydroxide (23 g, 0.58 mol) in water (200 mL). The reaction was stirred at room temperature for 20 minutes. The reaction was concentrated to half of the volume and acidified with 6 N aq. HCl. The mixture was extracted with CHCl3/i-PrOH (90:10) and the organic phase was concentrated under reduced pressure to get the title compound as a brown solid.

Workup

  1. concentrationThe reaction was concentrated to half of the volume
  2. extractionThe mixture was extracted with CHCl3/i-PrOH (90:10)
  3. concentrationthe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a3fec847502f49579489f56ed53ec9b1
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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