Sodium Hydroxide → HCID 21354847, compound

HRID 1360638Notes

Reaction equation

HRID 1360638 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[N:11][CH2:12][CH:13](OC)OC)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+]>S(=O)(=O)(O)O>[CH:1]([C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][CH:5]=1)[CH:10]=[N:11][CH:12]=[CH:13]2)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24786789HCID 24786789, compound

Product 1

HCID 21354847HCID 21354847, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-[(4-isopropylphenyl)methylene]-2,2-dimethoxyethanamine (5.0 g) was added to hot concentrated sulfuric acid (50 ml) at 140° C. dropwise over a period of 10 min. The mixture was stirred at this temperature for additional 10 min and cooled to RT. The mixture was basified with an aqueous solution of NaOH and the product was extracted with MTBE (6×75 ml). The combined organic layers were dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica (pet. ether/EtOAc 9/1) to afford the titled compound as a solid (200 mg, 15%). TLC—Chloroform/methanol: (9.5/0.5): Rf=0.55. 1H NMR (CDCl3, 400 MHz) δ 1.28 (6H, d), 3.10 (1H, m), 7.49 (1H, d), 7.53 (2H, m), 7.89 (1H, d), 8.49 (1H, d), 9.19 (1H, s).

Workup

  1. extractionthe product was extracted with MTBE (6×75 ml)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica (pet. ether/EtOAc 9/1)

Sources & evidence

ORD record
ord-cc3be87448a945fd88d6ccb14d1c0712
Source dataset
uspto-grants-2011_02
Patent number
US07879876B2

Reaction notes

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