Sodium Hydroxide → HCID 9923380, compound

HRID 2217058Notes

Reaction equation

HRID 2217058 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]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[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:17]=[C:18]([O:24][CH3:25])[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=2)=[O:15])=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 798124-PropoxybenzaldehydeHCID 959971-(3,5-Dimethoxyphenyl)ethan-1-one

Product 1

HCID 9923380HCID 9923380, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-propoxybenzaldehyde (0.5 g, 3.1 mmol) and 3,5-dimethoxyacetophenone (0.55 g, 3.1 mmol) in methanol (10 ml) was added 50% w/v of aqueous sodium hydroxide (2.4 ml, 0.031 mol). The reaction mixture was stirred for 2 h at room temperature and then extracted with ethyl acetate (3×20 ml), the combined organic layers were dried over magnesium sulphate and reduced in vacuo. The product was recrystallised from ethanol to give 0.978 g (93%) of off-white crystals. 1H-NMR (CDC3) δ 7.8 (d, 1H), 7.6(d, 2H), 7.3 (d, 1H), 7.15 (d, 2H), 6.9 (d, 2H), 6.65 (t, 1H), 4.0 (t, 2H), 3.9 (s, 6H), 1.85 (m, 2H), 1.05 (t, 3H). 13C-NMR (CDCl3) δ 190.2, 161.3, 160.8, 144.9, 140.6, 130.2, 127.4, 119.6, 114.9, 106.3, 104.8, 69.7, 55.6, 22.5, 10.4. Mass Spectrum m/e (M+1)327.

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. dry with materialthe combined organic layers were dried over magnesium sulphate
  3. customThe product was recrystallised from ethanol

Sources & evidence

ORD record
ord-936e34547eb046ca9c47a77d911a8007
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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