Hydrochloric Acid → HCID 20205029, compound

HRID 978073Notes

Reaction equation

HRID 978073 reaction equation
C([O:4][C:5]1[C:6]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:7]=2[S:8][C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)C.[OH-].[Na+].Cl>C(O)C>[CH2:10]([C:9]1[S:8][C:7]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:6]=2[C:5]=1[OH:4])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20205027HCID 20205027, compound

Product 1

HCID 20205029HCID 20205029, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-acetoxy-2-benzyl-5-chlorobenzo[b]thiophene (100 mg) and 2N aqueous sodium hydroxide (2 ml) in ethanol (1 ml) was heated at reflux temperature for 1 hour. The reaction mixture was cooled in an ice bath and acidifed with concentrated hydrochloric acid. The solid that separated out was collected by filtration, washed with water, and dried in vacuo over calcium sulfate to afford 2-benzyl-5-chloro-3-hydroxybenzo[b]thiophene as a white solid (40 mg); m/z 274 (M+.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 hour
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. customThe solid that separated out
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. dry with materialdried in vacuo over calcium sulfate

Sources & evidence

ORD record
ord-95e120158ab841e79a7c7eee09a83e3d
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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