Sodium Hydroxide → HCID 9881086, compound

HRID 2217059Notes

Reaction equation

HRID 2217059 reaction equation
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:14][C:15]([C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[CH:18]=1)=[O:16].[OH-].[Na+]>CO>[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9](/[CH:10]=[CH:14]/[C:15]([C:17]2[CH:18]=[C:19]([O:25][CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=2)=[O:16])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 798134-ButoxybenzaldehydeHCID 959971-(3,5-Dimethoxyphenyl)ethan-1-one

Product 1

HCID 9881086HCID 9881086, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-butoxybenzaldehyde (0.5 g, 2.8 mmol) and 3,5-dimethoxyacetophenone (0.5 g, 2.8 mmol) in methanol (10 ml) was added 50% w/v of aqueous sodium hydroxide (2.24 ml, 0.028 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 0.925 g (97%) of off-white crystals. 1H-NMR (CDCl3) δ 7.8 (d, 1H), 7.6 (d, 2H), 7.35 (d, 1H), 7.1 (d, 2H), 6.9 (d, 2H), 6.7 (t, 1H), 4.0 (t, 2H), 3.85 (s, 6H), 1.75 (m, 2H), 1.5 (m, 2H), 1.0 (t, 3H). 13C-NMR (CDCl3) δ 191.1, 161.4, 160.8, 144.9, 140.8, 130.2, 127.3, 119.6, 114.9, 106.3, 104.8, 67.9, 55.6, 31.2, 19.2, 13.8. Mass Spectrum m/e (M+1) 341.

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-fa79566c1a134bcd96f60190fdc8f34b
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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