Hydrochloric Acid → HCID 66673011, compound

HRID 422065Notes

Reaction equation

HRID 422065 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH3:11].[OH-].[Na+].[Cl:14][C:15]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.Cl>O.CCO>[Cl:14][C:15]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:16]=1/[CH:17]=[CH:9]/[C:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([CH3:11])[CH:4]=1)=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 357452,3-DichlorobenzaldehydeHCID 701354'-Hydroxy-3'-methylacetophenone

Product 1

HCID 66673011HCID 66673011, compoundYield 31.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 1-(4-hydroxy-3-methylphenyl)ethanone (0.7 g, 4.66 mmol) (ICC, Indofine Chemical Company Inc.) and NaOH (0.36 g, 9.1 mmol) in 10 mL of 200 proof EtOH was added 2,3-dichlorobenzaldehyde (0.8 g, 4.66 mmol) (ACROS). The reaction mixture was stirred at rt for 18 h. Upon completion by LC/MS, 5 mL of H2O was added and the reaction mixture was acidified with conc. HCl to pH 5-6. The resulting precipitate was filtered, washed with water and dried to yield (E)-3-(2,3-dichlorophenyl)-1-(4-hydroxy-3-methylphenyl)prop-2-en-1-one, (0.45 g, 31%). MS (EI) for C16H12C2O2, 308.3 (MH+).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-6857ccf7a6554c05a877257272f2caef
Source dataset
uspto-grants-2012_01
Patent number
US08101625B2

Reaction notes

Loading…