Ethanol → HCID 67174273, compound

HRID 2096434Notes

Reaction equation

HRID 2096434 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.CCO.[OH-].[Na+]>COC(C)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH:9]=[CH:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([Cl:12])[CH:14]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 114773-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 67174273HCID 67174273, compoundYield 347.6%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

In a bottle, 1-(5-bromo-2-hydroxyphenyl)ethanone (25 g, 0.02 mol), 3-chlorobenzaldehyde (16.35 g, 0.12 mol), EtOH (96%, 144 mL) and NaOH (42.1 g, 1.06 mol) were combined. The mixture was stirred vigorously for 0.5 h. 2-Methoxy-2-methylpropane (300 mL) was added and the mixture was filtered. The filtrate was poured into HCl (1 N, 800 mL) and filtered to give 1-(5-bromo-2-hydroxyphenyl)-3-(3-chlorophenyl) prop-2-en-1-one (23.47 g, 60%). 1H-NMR (CDCl3): 6.88 (d, 1H), 4.35 (m, 2H), 7.49 (m, 3H), 7.61 (s, 1H), 7.80 (m, 1H), 7.93 (m, 1H), 12.56 (s, 1H).

Workup

  1. filtrationthe mixture was filtered
  2. additionThe filtrate was poured into HCl (1 N, 800 mL)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-93aac8359c4d43f585e02724732980d0
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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