M-Cresol → (2R,3S,5R)-oxane-2,3,4,5-tetrol
Reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5]C=CC=1C.C1([OH:17])C=C(C)C=C(C)C=1.C=O.[C:20]([OH:25])(=O)[C:21]([OH:23])=[O:22]>COCCOCCOC>[OH:22][CH:21]1[O:23][CH2:1][C@@H:6]([OH:7])[C@H:5]([OH:17])[C@H:20]1[OH:25]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
M-cresol (338 g), 3,5-xylenol (229 g), diglyme (625 g), formaldehyde (37.3% in water, 603 g) and oxalic acid (1.13 g) were combined in a 5 liter flask and then heated at 95° C. for one hour. A mixture of m-cresol (338 g) and 3,5-xylenol (229 g) were added to the reaction mixture over one hour. 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=9.0; DR=2.88.
Workup
- additionwere added to the reaction mixture over one hour
- 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-648e50f571994cd7852dfd3dadbeb889
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05646218
Reaction notes
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