Formaldehyde → 4-Hydroxybutyraldehyde 2-hydroxytetrahydrofuran

Participants

Reaction Steps

The 4-hydroxybutyraldehyde/2-hydroxytetrahydrofuran was prepared by adding 5 parts of 2,3-dihydrofuran to 10 parts of 2% H2SO4 over about 20 minutes, keeping the temperature at 35° with cooling. The mixture was then neutralized with 30% NaOH. That mixture was mixed with 25 parts of water, 4.3 parts of 37% aqueous formaldehyde, 0.53 parts of 30% NaOH, and 2 parts of Raney nickel. Hydrogenation was then carried out at 27,576 kPa (gauge) hydrogen at 150° for 2 hours in a shaker tube. The organic portion of the resulting product consisted mainly of 1,4-butanediol and 2-methyl-1,4-butanediol, in a ratio of 25:75. There were also some unidentified higher boilers.

Provenance & Evidence