Hydrochloric Acid → 2-Carboxy-4-methoxy-3-(2-phenylethyl)benzo[b]thiophene

HRID 230883Notes

Reaction equation

HRID 230883 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[C:10]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:9]([C:20]([O:22]C)=[O:21])[S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.CO.[OH-].[Na+].Cl>O1CCCC1>[C:20]([C:9]1[S:8][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=2[C:10]=1[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 231035484-Methoxy-2-methoxycarbonyl-3-(2-phenylethyl)benzo[b]thiophene

Product 1

HCID 231035202-Carboxy-4-methoxy-3-(2-phenylethyl)benzo[b]thiopheneYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methoxy-2-methoxycarbonyl-3-(2-phenylethyl)benzo[b]thiophene (1.09 g) in tetrahydrofuran (6 mL)-methanol (21 mL) was added 1 mol/L aqueous sodium hydroxide solution (21 mL), and the mixture was heated for reflux for 3.5 hours. The reaction mixture was cooled to room temperature. To the mixture was added 2 mol/L hydrochloric acid (11 mL), and the precipitated crystals were collected by filtration. The crystals were dried under reduced pressure to give the title compound (1 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturefor reflux for 3.5 hours
  3. filtrationthe precipitated crystals were collected by filtration
  4. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-577da371a756430ebeb9460efc8effec
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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