Hydrochloric Acid → 1-(3-Chloro-2,4-dihydroxy-phenyl)ethanone

HRID 2244009Notes

Reaction equation

HRID 2244009 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[CH:8][C:9]=1[OH:10])=[O:3].[OH-].[Na+].[Cl:14][O-].[Na+].Cl>O>[Cl:14][C:8]1[C:9]([OH:10])=[C:4]([C:2](=[O:3])[CH3:1])[CH:5]=[CH:6][C:7]=1[OH:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69902',4'-DihydroxyacetophenoneHCID 14798Sodium HydroxideHCID 23665760Sodium Hypochlorite

Product 1

HCID 574382941-(3-Chloro-2,4-dihydroxy-phenyl)ethanoneYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,4,-dihydroxyacetophenone (6 g, 39.4 mmol), aqueous 1M sodium hydroxide (41.4 mL, 41.4 mmol) and water (200 mL) is stirred at room temperature. An aqueous 1.6M solution of sodium hypochlorite (32 mL) is added over a 1 hr period. The resulting dark brown solution is stirred 18 hr at room temperature. The reaction mixture is adjusted to a pH of 2-3 with concentrated aqueous hydrochloric acid. The resulting suspension is filtered and washed with water (4×100 mL). The filtered solid was dried under vacuum at 45° C. for 2.5 days to give the title compound (4.8 g, 65%) as a brown solid. LCMS 1 187 m+.

Workup

  1. filtrationThe resulting suspension is filtered
  2. washwashed with water (4×100 mL)
  3. customThe filtered solid was dried under vacuum at 45° C. for 2.5 days

Sources & evidence

ORD record
ord-c22923f54e514103b2325baf890581be
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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