Hydrochloric Acid → (3-Methyl-1,2-phenylene)dimethanol
Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[O:8][CH2:7]2.[BH4-].[Li+].Cl.C(OCC)(=O)C>O1CCCC1.CCCCCC>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH2:7][OH:8])[C:10]=1[CH2:9][OH:11]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
A solution of the 7-methyl-1(3H)-isobenzofuranone obtained above in tetrahydrofuran (80 ml) was cooled to 0° C., and lithium borohydride (1.90 g, 87.2 mmol) was added thereto. The mixture was stirred at 60° C. for 2 hours, then cooled to 0° C., and a 2N aqueous solution of hydrochloric acid (50 ml) was added dropwise. The product was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (75 g) column (eluent; ethyl acetate:hexane=2:1˜1:0) to afford the title compound (4.17 g, 19% total yield from methyl 2,6-dimethylbenzoate) as an oil.
Workup
- temperaturecooled to 0° C.
- extractionThe product was extracted with ethyl acetate
- customthe solvent was evaporated under reduced pressure
- customto give an oily residue
Sources & evidence
- ORD record
- ord-27b1a56507854675bcbefc3e56b414a1
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07230023B2
Reaction notes
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