Boron Trichloride → dimethyl 2-hydroxyisophthalate
Reaction equation
C[O:2][C:3]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].B(Cl)(Cl)Cl>>[OH:2][C:3]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]Participants
Procedure
A potassium salt of a phenol is needed for the next step in the reaction. The preferred potassium salt of a phenolic ester is made in two steps starting from commercially available 2-methoxyisophthalic acid. It is first reacted with trimethyloxonium tetrafluoroborate (Me3OBF4) and diisopropylethylamine ("iPr2NEt") under conditions effective to produce dimethyl 2-methoxyisophthalate. Gerecke, et al. Helv. Chim. Acta., 59:2551 (1976), which is hereby incorporated by reference. Then, the methyl ether is cleaved with BCl3 under conditions effective to yield dimethyl 2-hydroxyisophthalate. The potassium salt of dimethyl 2-hydroxyisophthalate is prepared by treating it with potassium hydride (KH) in toluene for about 20 minutes at about 0° C. under conditions effective to produce the potassium salt.
Sources & evidence
- ORD record
- ord-1fb37a5af479483fb88b5af35cb34b5c
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05808035
Reaction notes
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