Hydrochloric Acid → 2-(1-Benzothiophen-2-yl)acetic acid

HRID 408564Notes

Reaction equation

HRID 408564 reaction equation
[S:1]1[C:5]([CH2:6][C:7]#N)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[OH-:13].[Na+].Cl.CCO.[OH2:19]>>[S:1]1[C:5]([CH2:6][C:7]([OH:19])=[O:13])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 126319232-(1-Benzothiophen-2-yl)acetonitrileHCID 19096565Water ethanol

Product 1

HCID 127650652-(1-Benzothiophen-2-yl)acetic acid

Conditions

Temperature
80 °C

Procedure

To a solution of benzo[b]thiophen-2-yl-acetonitrile (1 eq.) in EtOH/water (1/1) was added NaOH pellets (12 eq.). The reaction was heated at 80° C. for 4 h and then allowed to cooled down to 20° C., at which point concentrated HCl was added carefully until pH=7 was reached. The reaction mixture was partially concentrated under reduced pressure then partitioned between water and EtOAc. The aqueous layer was extracted three times with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford benzo[b]thiophen-2-yl-acetic acid.

Workup

  1. additionwas added carefully until pH=7
  2. concentrationThe reaction mixture was partially concentrated under reduced pressure
  3. customthen partitioned between water and EtOAc
  4. extractionThe aqueous layer was extracted three times with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b463061a0290425c902cf6b385f0a158
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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