Hydrochloric Acid → 2-Dibenzothiophenecarboxylic acid

HRID 1447556Notes

Reaction equation

HRID 1447556 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1)(=[O:3])C.Cl[O-:18].[Na+].[OH-].[Na+].Cl>O1CCOCC1>[CH:5]1[C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[S:8][C:7]=2[CH:15]=[CH:16][C:4]=1[C:1]([OH:3])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3120271-(Dibenzo[b,d]thiophen-2-yl)ethan-1-oneHCID 23665760Sodium Hypochlorite

Product 1

HCID 32900242-Dibenzothiophenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Acetyldibenzothiophene (2.24 g.), sodium hypochlorite solution, (47 ml. containing 5.7% available chlorine), normal sodium hydroxide solution (50 ml.) and dioxan (50 ml.), were heated on a steam bath with stirring for 5 hr. The mixture was acidified with excess hydrochloric acid, and the precipitated colourless solid filtered off, washed with water, and recrystallise twice from acetic acid to give dibenzothiophene-2-carboxylic acid, m.pt. 281°-283° C.

Workup

  1. filtrationthe precipitated colourless solid filtered off
  2. washwashed with water
  3. customrecrystallise twice from acetic acid

Sources & evidence

ORD record
ord-bf629dc09eae41ee987521bc0f2012f1
Source dataset
uspto-grants-1979_12
Patent number
US04177257

Reaction notes

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