Hydrochloric Acid → 2-Hydroxy-1,2-bis(3-hydroxyphenyl)ethanone

HRID 1414174Notes

Reaction equation

HRID 1414174 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=[O:11])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl.C(Cl)(Cl)Cl.CO>O.[Sn]>[OH:9][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1)[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1)=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13158606Bis(3-hydroxyphenyl)ethane-1,2-dioneHCID 21584188Chloroform methanol

Product 1

HCID 205128182-Hydroxy-1,2-bis(3-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5352426Tin atomSolvent

Procedure

To a hot stirred solution of 3,3'-dihydroxybenzil (5 g.) in water (200 ml) and tin (30 mesh) was slowly added concentrated hydrochloric acid (10 ml.). Heating on a steam bath with efficient mechanical stirring was continued for 1 hour. Thin layer chromatography on Silica AR 7GF plates (Mallinckrodt) with chloroform-methanol (9:1) showed the reaction was largely complete after 15 minutes. The mixture was filtered, while hot, through Celite and the filtrate was evaporated to smaller volume. The resulting crystals (4.60 g.), m.p. 159°-162° were recrystallized from hot water with decolorization to give white crystals, m.p. 173°-175°, M+ 244 (E. I. mode), pmr (DMSO-d6) δ 5.97 [s, --CH(OH)].

Workup

  1. temperatureHeating on a steam bath with efficient
  2. waitwas largely complete after 15 minutes
  3. filtrationThe mixture was filtered
  4. customwhile hot, through Celite and the filtrate was evaporated to smaller volume
  5. customThe resulting crystals (4.60 g.), m.p. 159°-162° were recrystallized from hot water with decolorization
  6. customto give white crystals, m.p. 173°-175°, M+ 244 (E. I. mode), pmr (DMSO-d6)

Sources & evidence

ORD record
ord-46f8bd68555e4ed9a83966d34c12d9c7
Source dataset
uspto-grants-1977_01
Patent number
US04001216

Reaction notes

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