Sodium Hydroxide → HCID 10132918, compound

HRID 2217065Notes

Reaction equation

HRID 2217065 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=O.[CH3:15][C:16]([C:18]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[CH:19]=1)=[O:17].[OH-].[Na+]>CO>[OH:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:15]/[C:16]([C:18]2[CH:19]=[C:20]([O:26][CH3:27])[CH:21]=[C:22]([O:24][CH3:25])[CH:23]=2)=[O:17])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 959971-(3,5-Dimethoxyphenyl)ethan-1-oneHCID 21946174HCID 21946174, compound

Product 1

HCID 10132918HCID 10132918, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-hydroxy-4-butoxybenzaldehyde (0.4 g, 2.1 mmol), 3,5-dimethoxyacetophenone (0.371.9, 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 0.36 g (50%) of a yellow solid: 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.3 (m, 2H), 7.1 (d, 3H), 6.8 (d, 1H), 6.7 (t, 1H), 5.7 (s, 1H), 4.1 (t, 2H), 3.9 (s, 6H), 1.8 (m, 2H), 1.5 (m, 2H), 1.0 (t, 3H). 13C-NMR (CDCl3) δ 190.0, 160.9, 148.3, 146.0, 144.9, 140.5, 128.4, 122.6, 120.2, 112.9, 111.4, 106.2, 104.9, 68.8, 55.6, 31.1, 19.1. 13.7. Mass Spectrum m/e (M+1) 357. Anal. Calcd. for C21H24O5: C, 70.77, H, 6.79. Found C, 70.84; H, 6.81.

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-4e517f95742e4ecba09c70d2ffc46d59
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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