Pyridine → Methyl 2-methyl-2-phenylpropanoate
Reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].N1C=CC=CC=1.[C:18](OC(=O)C)(=[O:20])C.C(OCC)(=O)C>O>[CH3:5][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:1])[C:3]([O:20][CH3:18])=[O:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-methyl-2-phenyl-propanol (Intermediate 3) (0.5 kg) and pyridine (268 ml) were charged to a reactor and chilled to 0° C. Acetic anhydride (680 gms) was slowly added through a dropper at 10-20° C. The mixture was stirred for 2 hours at 10-20° C. Ethyl acetate (1.5 ltr) was added and chilled water (2 ltrs) was slowly added through a dropper at 10-20° C. The mixture was stirred for ½ hr. The ethyl acetate layer was separated and 10% chilled dilute HCl was added. The ethyl acetate layer was then washed with sodium bicarbonate until a pH of 7 was obtained. The ethyl acetate layer was dried with sodium sulphate and concentrated under vacuum. The resulting oil was distilled under vacuum (15 mm of Hg), at 80-100° C.
Workup
- additionwas slowly added through a dropper at 10-20° C
- stirringThe mixture was stirred for ½ hr
- customThe ethyl acetate layer was separated
- temperature10% chilled dilute HCl
- additionwas added
- washThe ethyl acetate layer was then washed with sodium bicarbonate until a pH of 7
- customwas obtained
- dry with materialThe ethyl acetate layer was dried with sodium sulphate
- concentrationconcentrated under vacuum
- distillationThe resulting oil was distilled under vacuum (15 mm of Hg), at 80-100° C.
Sources & evidence
- ORD record
- ord-62adbe02b7274e31b61f46d29ffd970f
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247434B2
Reaction notes
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