1.1- Dimethoxy-3-nitropropane

NITROPROPANAL, 3-NITROPROPANOL, AND 3-NITROPROPANAL DIMETHYL ACETAL (Propanal, 3-nitro- 1-Propanol, 3-nltro- and Propane, 1,l-dimethoxy-3-nitro-)... 

Nitropropanal dimethyl acetal Propane, 1,1-dimethoxy-3-nitro- (10) (72447-81-5) Sodium nitrite Nitrous acid sodium salt (8,9) (7632-00-0)... 

SYNTHESIS In 50 mL of benzene there was dissolved 31.6 g 2,5-dimethoxy-4-methylbenzaldehyde (see recipe for 2C-D for its preparation), 20.2 mL 1-nitropropane, and 6 mL cyclohexylamine. This solution was held at reflux in a Dean Stark apparatus for 24 h, effectively removing the water of reaction. Upon cooling, there was deposited 19.6 g of 1 -(2,5-dimethoxy-4-methylphenyl)-2-nitro-1 -butene as brilliant orange crystals. The mp, after recrystallization from MeOH, was 114-115 °C and a second recrystallization increased the mp another 2 °C. Anal. 

A mixture of 31.6 g. of 2,5-dimethoxy-4-methylbenzaldehyde, 20.2 mL. of 1-nitropropane, 6 mL. cyclohexylamine, and 50 mL. benzene is kept at reflux in a Dean Stark apparatus for 24 hours. Cooling results in tbe spontaneous crystallization of an orange product wbicb on filtration and drying weighs 14.9 g. Recrystallization from methanol yields the product 2-nitro-(2,5-dimethoxy-4-methylphenyl)-butene-l as an orange crystalline material, mp. 115°C. Source Shulgin 1976... 

NITROPROPANAL DIMETHYL ACETAL PROPANE, 1,1-DIMETHOXY-3-NITRO- (72447-81-5), 77. 236... 

ARIADNE itself, reduced not with LAH or AH (which would give the primary amine), but rather with sodium borohydride and borane dimethylsulfide. The product, 1-(2,5-dimethoxy-4-methylphenyl)-N-hydroxy-2-aminobutane hydrochloride, was a white crystalline material. The TOM analogue got as far as the nitrostyrene. This was made from 2-methoxy-4-methyl-5-(methylthio)benzaldehyde (see under the 5-TOM recipe for its preparation) and nitropropane in acetic acid, and gave bright yellow crystals. The true pseudo-analogue is the 2,4,6-trimethoxy material based on TMA-6, which is the "real" pseudo-TMA-2. The nitrostyrene from 2,4,6-trimethoxybenzaldehyde and nitropropane crystallized from MeOH/CH3CN as fine yellow crystals, and this was reduced with AH in cold THF to 1-(2,4,6-trimethoxyphenyl)-2-aminobutane which was a bright, white powder. 

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