3-Methoxyacetophenone → HCID 9944035, compound

HRID 2217075Notes

Reaction equation

HRID 2217075 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[CH3:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)=[O:15].[OH-].[Na+]>CO>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[CH:13]/[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[O:15])=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 114603-MethoxyacetophenoneHCID 14798Sodium HydroxideHCID 798124-Propoxybenzaldehyde

Product 1

HCID 9944035HCID 9944035, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-propoxybenzaldehyde (1 g, 6.09 mmol) and 3-methoxyacetophenone (0.91 g, 6.09 mmol) in methanol (30 ml) was added 50% w/v solution of aqueous sodium hydroxide (9.7 ml, 0.122 mol). The reaction mixture was stirred at room temperature for 24 h. A precipitate was isolated by filtration, washed with cold methanol and subsequently recrystallised from methanol to afford 0.38 g (21%) of pale yellow crystals. 1H-NMR δ (CDCl3), 1.6 (t, 3H), 1.85 (m, 2H), 3.9 (s, 2H), 3.95 (t, 2H), 6.9 (d, 2H), 7.1 (1H), 7.38 (m, 2H), 7.55 (m, 4H), 7.8 (d, 1H). 13C-NMR (CDCl3) δ 190.3, 161.3, 159.9, 139.9, 127.4, 69.6, 22.5. Mass Spectrum m/e (M+1) 297. Anal. Calcd. for C19H20O3: C, 77.00; H, 6.80. Found C, 76.86; H, 6.94.

Workup

  1. customA precipitate was isolated by filtration
  2. washwashed with cold methanol
  3. customsubsequently recrystallised from methanol

Sources & evidence

ORD record
ord-d8f64036f2364994a31e01a1ddbfcd57
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

Loading…