3-Methoxyacetophenone → HCID 57799938, compound

HRID 2100649Notes

Reaction equation

HRID 2100649 reaction equation
[F:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)=[O:13]>[OH-].[Na+]>[F:1][C:2]1[C:3]([CH3:10])=[C:4](/[CH:5]=[CH:11]/[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 114603-MethoxyacetophenoneHCID 27792353-Fluoro-2-methylbenzaldehyde

Product 1

HCID 57799938HCID 57799938, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
21.5 °C

Procedure

To a stirred solution of 3-fluoro-2-methylbenzaldehyde (150 g, 1.2 mol) in IMS (600 mL) was added 3-methoxyacetophenone (163 g, 1.2 mol). NaOH (10% aq, 750 mL) was added over 40 min using a water bath to maintain a temperature between 18-25° C. The mixture was stirred vigorously at room temperature for 15 h and a thick precipitate was formed. The solid was isolated by filtration, broken up with a mortar and pestle, and washed IMS and water. After drying at 45° C. for 48 h, 273 g (84% yield), the desired product (E)-3-(3-fluoro-2-methylphenyl)-1-(3-methoxyphenyl)prop-2-en-1-one was obtained (characterized by LCMS and 1H NMR, LRMS (M+H+) m/z=271.1.

Workup

  1. customa thick precipitate was formed
  2. customThe solid was isolated by filtration
  3. washwashed IMS and water
  4. customAfter drying at 45° C. for 48 h

Sources & evidence

ORD record
ord-eb6f47128bae45a7a33cf84ea90ac31f
Source dataset
uspto-grants-2009_08
Patent number
US07572814B2

Reaction notes

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