6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene → 2-(4-Hydroxyphenyl)benzo(b)thiophen-6-ol

HRID 2163320Notes

Reaction equation

HRID 2163320 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([O:18]C)[CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 10176127Pyridinium chloride

Product 1

HCID 4459202-(4-Hydroxyphenyl)benzo(b)thiophen-6-olYield 71%

Conditions

Temperature
220 °C

Procedure

A mixture of 16.5 grams of 2-(4-methoxyphenyl)-6-methoxybenzothiophene and 50 grams of pyridine hydrochloride was prepared. The mixture was heated at 220° C. for six hours. The resulting mixture then was poured into an ice-water mixture. The mixture was filtered, and the collected solid was dried in air and recrystallized from methanol to obtain 10.5 grams of 2-(4-hydroxyphenyl)-6-hydroxybenzothiophene, melting point 305°-306° C.

Workup

  1. customwas prepared
  2. filtrationThe mixture was filtered
  3. customthe collected solid was dried in air
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2f00f6aeee354a4cb636cccd84096a57
Source dataset
uspto-grants-1979_01
Patent number
US04133814

Reaction notes

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