Acetophenone → 3-bromobenzalacetophenone

HRID 1831876Notes

Reaction equation

HRID 1831876 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O>O.CO.C(O)C>[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[CH:4][C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

7

Reactant 3

HCID 7410Acetophenone2×HCID 14798Sodium HydroxideHCID 765833-Bromobenzaldehyde

Product 1

HCID 3673183-bromobenzalacetophenoneYield 75.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (12.00 g, 300 mmol) and acetophenone (24 g, 200 mmol) were dissolved in water (90 mL) and methanol (300 mL). 3-Bromobenzaldehyde (37 g, 200 mmol) dissolved in ethanol (50 mL) was added dropwise to the acetophenone solution. A slurry quickly formed, which was allowed to two additional hours. The slurry was filtered, was with water until the filtrate was neutral to pH paper, and dried at 80° C. for 12 hours. Light yellow crystals were obtained (43.4 g, 75.6% yield).

Workup

  1. customA slurry quickly formed
  2. filtrationThe slurry was filtered
  3. customdried at 80° C. for 12 hours
  4. customLight yellow crystals were obtained (43.4 g, 75.6% yield)

Sources & evidence

ORD record
ord-1f480a235e3a4c4684ce30f3df6b117d
Source dataset
uspto-grants-2006_06
Patent number
US07067702B2

Reaction notes

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