Sodium Hydroxide → HCID 10268251, compound

HRID 2217077Notes

Reaction equation

HRID 2217077 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[C:23](=[O:25])[CH3:24].[OH-].[Na+]>CO>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[CH:24]/[C:23]([C:16]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=2[O:14][CH3:13])=[O:25])=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 709912',5'-DimethoxyacetophenoneHCID 798124-Propoxybenzaldehyde

Product 1

HCID 10268251HCID 10268251, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-propoxybenzaldehyde (1 g, 6.1 mmol) and 2′,5′-dimethoxyacetophenone (1.1 g, 6.1 mmol) in methanol (15 ml) was added 50% w/v solution of aqueous sodium hydroxide (9.7 ml, 0.122 mol). The reaction mixture was stirred at room temperature for 18 h. A precipitate was isolated by filtration and subsequently recrystallised from ethanol to afford 0.97 g (49%) of pale yellow crystals. 1H-NMR (CDCl3) δ 1.0 (t, 3H), 1.8 (m, 2H), 3.7 (s, 3H), 3.8 (s, 3H), 3.9 (t, 2H), 6.9 (m, 3H), 6.9 (d, 1H) 7.15 (d, 1H), 7.25 (d, 1H), 7.5 (m, 3H), 13C-NMR (CDCl3) δ 192.59, 160.86,161.11, 153.59, 152.34, 130.07, 127.56, 22.47. Mass Spectrum m/e (M+1) 327. Anal. Calcd. for C20H2O4: C, 73.62; H, 6.75. Found C, 73.55; H, 6.88.

Workup

  1. customA precipitate was isolated by filtration
  2. customsubsequently recrystallised from ethanol

Sources & evidence

ORD record
ord-c67b6e233bbb407d9b57a5b411df6caf
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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