Sodium Hydroxide → HCID 10131466, compound

HRID 2217061Notes

Reaction equation

HRID 2217061 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH:5]=O.[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>[OH:1][C:2]1[CH:3]=[C:4](/[CH:5]=[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:8][C:9]=1[O:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 756794-Ethoxy-3-hydroxybenzaldehydeHCID 959971-(3,5-Dimethoxyphenyl)ethan-1-one

Product 1

HCID 10131466HCID 10131466, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-hydroxy-4-ethoxybenzaldehyde (0.413 g, 2.5 mmol), 3,5-dimethoxyacetophenone (0.448 mg, 2.5 mmol) and 50% w/v of aqueous sodium hydroxide (3.98 ml, 0.049 mol) in methanol (5 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 by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) yielded 0.29 g (36%) of a yellow solid. 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.2 (m, 2H), 7.1 (d, 3H), 6.8 (d, 1H), 6.5 (t, 1H), 5.7 (s, 1H), 4.1 (q, 2H), 3.9 (s, 6H), 1.4 (t, 3H). 13C-NMR (CDCl3) δ 190.1, 160.9, 148.2, 146.1, 144.9, 140.6, 128.5, 122.7, 120.3, 113.1, 111.4, 106.3, 105.0, 64.7, 55.7, 14.8. Mass Spectrum m/e (M+1) 329. Anal. Calcd. for C19H20O5.0.5H2O: C, 69.5; H, 6.14. Found C, 69.62; H, 6.16.

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 by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate)

Sources & evidence

ORD record
ord-f7f1e6bd952f4eb7b3f732c1fd016e34
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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