Hydrochloric Acid → 2-Hydroxy-1,2-bis(4-hydroxyphenyl)ethan-1-one

HRID 1164246Notes

Reaction equation

HRID 1164246 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21]COC)=[CH:17][CH:16]=2)[OH:14])=[O:12])=[CH:7][CH:6]=1.Cl.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[NH4+].[NH4+]>O.C(O)C>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([CH:13]([C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)[OH:14])=[O:12])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 6097028Ammonium SulfateHCID 23513120HCID 23513120, compound

Product 1

HCID 157928282-Hydroxy-1,2-bis(4-hydroxyphenyl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

4,4'-Di(methoxymethoxy)benzoin (26 g) was dissolved in a mixture of water (250 ml) and ethanol (250 ml) at 80°. Concentrated hydrochloric acid (2.6 g) was added, and the solution was stirred at 80° for 45 minutes. Then it was cooled and a solution of sodium bicarbonate (2.6 g) in water (50 ml) was added. The reaction mixture was poured into water (600 ml) saturated with ammonium sulphate, and the resulting mixture was extracted with ether. The ethereal solution was dried over anhydrous MgSO4, and removal of the ether by distillation left 19 g of a dark red solid. Thin layer chromatography of this showed it to be substantially 4,4'-dihydroxybenzoin by comparison with an authentic sample (see later), and the material was used without further purification.

Workup

  1. temperatureThen it was cooled
  2. extractionthe resulting mixture was extracted with ether
  3. dry with materialThe ethereal solution was dried over anhydrous MgSO4, and removal of the ether by distillation
  4. waitleft 19 g of a dark red solid
  5. customwas used without further purification

Sources & evidence

ORD record
ord-488c92c2578f4124839f179ef150c6c6
Source dataset
uspto-grants-1983_01
Patent number
US04368253

Reaction notes

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