3',4',5'-Trimethoxyacetophenone → HCID 10156010, compound

HRID 2217068Notes

Reaction equation

HRID 2217068 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])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[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:27][CH3:28])[C:20]([O:25][CH3:26])=[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 143453',4',5'-TrimethoxyacetophenoneHCID 14798Sodium HydroxideHCID 798134-Butoxybenzaldehyde

Product 1

HCID 10156010HCID 10156010, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-butoxybenzaldehyde (1.64 ml, 9.5 mmol) and 3,4,5-trimethoxyacetophenone (2.0 g, 9.5 mmol) in methanol (30 ml) was added 50% w/v of aqueous sodium hydroxide (7.6 ml, 0.095 mol). The reaction was stirred for 24 h at room temperature. A precipitate was isolated by filtration, washed with pet:ether and subsequently recrystallised from ethanol to give 3.0 g (85%) of a pale yellow powder. 1H-NMR (CDCl3) δ 7.8 (d, 1H), 7.6 (d, 2H), 7.4 (d, 1H), 7.25 (d, 2H), 7.0 (d, 2H), 4.05 (t, 2H), 4.0 (s×2, 9H), 1.8 (m, 2H), 1.5 (m, 2H), 1.0 (t, 3H). Mass Spectrum m/e (M+1) 370.

Workup

  1. customA precipitate was isolated by filtration
  2. washwashed with pet
  3. customether and subsequently recrystallised from ethanol

Sources & evidence

ORD record
ord-6d9fb5e0ea7f4d38a688de0dc11b419a
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

Loading…