Hexamethylenetetramine → 4,4-Dimethoxy-2-methylbut-2-enal

HRID 129979Notes

Reaction equation

HRID 129979 reaction equation
Br[CH2:2][CH:3]=[C:4](C)[CH:5]([O:8][CH3:9])[O:6][CH3:7].C1N2CN3CN(C2)CN1C3.[Cl-].[Na+].[CH:23]([O:26]C(C)C)(C)C>O>[CH3:9][O:8][CH:5]([O:6][CH3:7])[CH:4]=[C:3]([CH3:2])[CH:23]=[O:26]

Participants

6

Reactant 4

HCID 4101HexamethylenetetramineHCID 5234Sodium ChlorideHCID 7914Diisopropyl EtherHCID 53862214HCID 53862214, compound

Product 1

HCID 543587234,4-Dimethoxy-2-methylbut-2-enalYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Bromo-1,1-dimethoxy-2-methyl-2-butene (2 g) was added to a solution of hexamine (1.7 g) and water (10 ml), and the mixture was stirred at room temperature for 14 hours. Dowex 50×8 (type H)(3 g) was previously treated with sodium chloride to convert it to type Na. Then isopropyl ether (20 ml) was added to the above reaction mixture, the type Na resin was added, and the mixture was stirred at 70° C. for 6 hours. The isopropyl ether layer was separated, concentrated and purified by column chromatography to give 4,4-dimethoxy-2-methyl-2-buten-1-al (0.92 g, 64%).

Workup

  1. additionthe type Na resin was added
  2. stirringthe mixture was stirred at 70° C. for 6 hours
  3. customThe isopropyl ether layer was separated
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-14c9aad48624413d905738f079d73073
Source dataset
uspto-grants-1995_11
Patent number
US05471004

Reaction notes

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