Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Bromo-2,6-dimethylphenol | HCID 16919 | — |
| Reactant | 2-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol | HCID 14001295 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 89825893 | HCID 89825893 | 70% |
Reaction Steps
4-Bromo-2,6-dimethylphenol (2.00 g, 9.95 mmol), toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester (Intermediate 10, 2.83 g, 10.9 mmol) and potassium carbonate (1.01 g, 10.9 mmol) are combined in N,N-dimethylformamide (50 mL) and heated at 80° C. for 24 hours. The mixture is cooled, poured into water and extracted with diethyl ether. The organic phase is dried and the solvent removed. The residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane) to give the title compound (Yield 2.00 g). GC (METHOD 1): tR=11.26 min; Mass spectrum (EI+): m/z=286/288 [M]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09308194B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-b82e9098c83c48a38056fe2c6e34e2c8 |
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| Source note | uspto-grants-2016_04 |
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