Sodium Hydroxide → (e)-1-(3-Hydroxy-4-propoxyphenyl)-3-(3,5-dimethoxyphenyl)prop-1-en-3-one

HRID 2217063Notes

Reaction equation

HRID 2217063 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH3:13])[CH:5]=O.[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>[OH:1][C:2]1[CH:3]=[C:4](/[CH:5]=[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:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 959971-(3,5-Dimethoxyphenyl)ethan-1-oneHCID 219461763-Hydroxy-4-propoxybenzaldehyde

Product 1

HCID 9967877(e)-1-(3-Hydroxy-4-propoxyphenyl)-3-(3,5-dimethoxyphenyl)prop-1-en-3-oneYield 132.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-hydroxy-4-propoxybenzaldehyde (0.4 g, 2.1 mmol), 3,5-dimethoxyacetophenone (0.371 mg, 2.1 mmol) and 50% w/v of aqueous sodium hydroxide (3.3 ml, 0.206 mol) in methanol (10 ml) at room temperature for 18 h. The yellow solid that precipitated was filtered and sequentially washed with cold methanol and ether and finally dried in a vacuum dessicator. Purification was achieved using column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) which gave 0.95 g (19%) of a yellow solid. 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.3 (m, 2H), 7.1 (d, 3H), 6.8 (d, 1H), 6.6 (d, 1H), 5.7 (s, 1H), 4.1 (t, 2H), 3.9 (s, 6H), 1.9 (m, 2H), 1.0 (t, 3H). 13C-NMR (CDCl3) δ 160.9, 146.0, 144.9, 128.4, 122.6, 120.2, 112.9, 106.2, 104.9, 70.6, 55.6, 22.4, 10.4. Mass Spectrum m/e (M+1) 343. Anal. Calcd. for C20H22O5: C, 70.16; H, 6.48. Found C, 70.08; H, 6.38.

Workup

  1. filtrationThe yellow solid that precipitated was filtered
  2. washsequentially washed with cold methanol and ether
  3. customfinally dried in a vacuum dessicator
  4. customPurification

Sources & evidence

ORD record
ord-9dab6cf371a745b1883ada18bafbe116
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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