Hydrochloric Acid → HCID 23444738, compound

HRID 1841372Notes

Reaction equation

HRID 1841372 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH:17]=O.[OH-].[Na+].Cl>O.C(O)C>[Br:1][C:2]1[C:3]([OH:12])=[C:4]([C:9](=[O:11])/[CH:10]=[CH:17]/[C:16]2[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:14]([Cl:13])[CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 786193-Chloro-4-methoxybenzaldehydeHCID 111389181-(3-Bromo-2-hydroxy-5-methylphenyl)ethan-1-one

Product 1

HCID 23444738HCID 23444738, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(3-Bromo-2-hydroxy-5-methylphenyl)-1-ethanone (10 g, 43.7 mmol) and 3-chloro-4-methoxybenzaldehyde (9.0 g, 1.2 molar eq.) were introduced into 80% aqueous ethanol solution (150 ml), sodium hydroxide (NaOH; 5.2 g, 3.0 molar eq.) was added thereto, and the resulting mixture was stirred for 17 hours at room temperature. After completion of reaction, the reaction solution was neutralized by 2N aqueous hydrochloric acid solution and diluted with water (150 ml). The yellow solid thus precipitated was washed with water and methanol to give 14.2 g (Yield 85%) of the purified title compound.

Workup

  1. additionwas added
  2. customAfter completion of reaction
  3. customThe yellow solid thus precipitated
  4. washwas washed with water and methanol
  5. customto give 14.2 g (Yield 85%) of the
  6. custompurified title compound

Sources & evidence

ORD record
ord-8a84eb9731bb4821b36f2614057d40e2
Source dataset
uspto-grants-2004_01
Patent number
US06683095B2

Reaction notes

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