O1C=CCC1.OS(O)(=O)=O.[OH-].[Na+].[OH:13][CH2:14][CH2:15][CH2:16][CH:17]=[O:18].[OH:19][CH:20]1[CH2:24][CH2:23][CH2:22][O:21]1.C=O.[H][H].C(O)CCCO.CC(CCO)CO>[Ni].O>[OH:18][CH2:17][CH2:16][CH2:15][CH:14]=[O:13].[OH:19][CH:20]1[CH2:24][CH2:23][CH2:22][O:21]1
The 4-hydroxybutyraldehyde/2-hydroxytetrahydrofuran was prepared by adding 20 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. The organic portion of the resulting homogeneous product was a 2:1 mixture of 4-hydroxybutyraldehyde and its cyclic hemiacetal, 2-hydroxytetrahydrofuran. Thirty parts of that mixture were mixed with 10 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 55:45. There were also some unidentified higher boilers.
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