Sodium Bicarbonate → 2-Hydroxymethyl-2,4,6,7-tetramethyldihydrobenzofuran
Reaction equation
[CH3:1][C:2](=[CH2:14])[CH2:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH3:11])=[C:6]([CH3:12])[C:5]=1[OH:13].C(=O)([O-])[OH:16].[Na+]>C(Cl)Cl>[OH:16][CH2:14][C:2]1([CH3:1])[CH2:3][CH:4]2[CH:9]([CH3:10])[CH:8]=[C:7]([CH3:11])[C:6]([CH3:12])=[C:5]2[O:13]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
31.86 g of 2-(2-methyl-2-propenyl)-3,5,6-trimethylphenol was dissolved in 600 ml of methylene chloride and 47.5 g of methchloroperbenzoic acid was gradually charged while maintaining at 0° C. After stirring at 0° C. for 2 hours, the solution was poured into an aqueous sodium hydrogen carbonate. The organic layer was extracted with chloroform, washed with an aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate and, after the solvent was distilled off, the residue was purified by silica gel column chromatography (chloroform) to obtain 17 g of the objective product.
Workup
- extractionThe organic layer was extracted with chloroform
- washwashed with an aqueous saturated sodium hydrogen carbonate solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationafter the solvent was distilled off
- customthe residue was purified by silica gel column chromatography (chloroform)
Sources & evidence
- ORD record
- ord-2f833f6ed1534ae9b596ad94690411f9
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07553837B2
Reaction notes
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