Hydrochloric Acid → HCID 20205056, compound

HRID 978089Notes

Reaction equation

HRID 978089 reaction equation
C([O:4][C:5]1[C:6]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:7]=2[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)C.[OH-].[Na+].Cl>>[Cl:20][C:18]1[CH:17]=[CH:16][C:7]2[S:8][C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:5]([OH:4])[C:6]=2[CH:19]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13787731HCID 13787731, compound

Product 1

HCID 20205056HCID 20205056, compound

Procedure

A mixture of 3-acetoxy-5-chloro-2-phenylbenzo[b]thiophene (150 mg, 0.50 mmol) and 20% aqueous sodium hydroxide (5 ml) was stirred at reflux temperature for 1 hour. The cooled reaction mixture was acidified with concentrated hydrochloric acid, the solid that separated out filtered, washed with water, and dried in vacuo over phosphorous pentoxide. Recrystallization from cyclohexane afforded pure 5-chloro-3-hydroxy-2-phenylbenzo[b]thiophene; yield 35 mg (26%); m/z 275 (M+.).

Workup

  1. temperatureat reflux temperature for 1 hour
  2. customThe cooled reaction mixture
  3. customthe solid that separated
  4. filtrationout filtered
  5. washwashed with water
  6. dry with materialdried in vacuo over phosphorous pentoxide
  7. customRecrystallization from cyclohexane afforded pure 5-chloro-3-hydroxy-2-phenylbenzo[b]thiophene

Sources & evidence

ORD record
ord-6f36d33a632c48679a6fc3e576fe38a0
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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