M-Cresol → (2R,3S,5R)-oxane-2,3,4,5-tetrol
Reaction equation
C1[C:6]([OH:7])=CC=CC=1C.C1([OH:17])C=C(C)C=C(C)C=1.C1(=O)OC(=O)C=C1.C[O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32]C>>[OH:17][CH:30]1[O:29][CH2:28][C@@H:27]([OH:26])[C@H:6]([OH:7])[C@H:31]1[OH:32]Participants
5
Conditions
- Temperature
- 95 °C
Procedure
M-cresol (114 g), 3,5-xylenol (42.8 g), diglyme (50.0), and maleic anhydride (3.13 g) were combined in a flask and heated to 95° C. The solution was purged with nitrogen for 3 minutes. Formaldehyde (37.2% in water, 83.7 g) was added slowly over 75 minutes. Heating at 95° C. was continued for four hours. The volatile components were distilled away from the reaction mixture until the residue was at 200° C. Vacuum was applied slowly to the distillation until 35 mmHg and 220° C. were both reached. The novolak resin in the reaction flask was then cooled to room temperature. RMW=9.2; DR=10.4.
Workup
- customThe solution was purged with nitrogen for 3 minutes
- additionFormaldehyde (37.2% in water, 83.7 g) was added slowly over 75 minutes
- temperatureHeating at 95° C.
- distillationThe volatile components were distilled away from the reaction mixture until the residue
- customwas at 200° C
- distillationVacuum was applied slowly to the distillation until 35 mmHg and 220° C.
- temperatureThe novolak resin in the reaction flask was then cooled to room temperature
Sources & evidence
- ORD record
- ord-7ede0d670d7744fd9167642a536d8a56
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05646218
Reaction notes
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