Sodium Hydroxide → HCID 9857932, compound

HRID 2217057Notes

Reaction equation

HRID 2217057 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:2].[CH3:12][C:13]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=1)=[O:14].[OH-].[Na+]>CO>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[CH:12]/[C:13]([C:15]2[CH:16]=[C:17]([O:23][CH3:24])[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=2)=[O:14])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 248344-EthoxybenzaldehydeHCID 959971-(3,5-Dimethoxyphenyl)ethan-1-one

Product 1

HCID 9857932HCID 9857932, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-ethoxybenzaldehyde (1.0 g, 6.6 mmol) and 3,5-dimethoxyacetophenone (1.19 g, 6.6 mmol) in methanol (10 ml) was added 50% w/v of aqueous sodium hydroxide (5.3 ml, 0.06 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 and the product was recrystallised from ethanol to give 1.12 g (74%) of yellow crystals. 1H-NMR (CDCl3) 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 (q, 2H), 3.8 (s, 6H), 1.4 (t, 3H). 13C-NMR (CDCl3) δ 190.1, 161.1, 160.8, 140.6, 127.4, 63.6. Mass Spectrum m/e (M+1) 313.

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-0186e84cf43e49deb32745c95f54e48e
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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