Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | 2,5-Dimethylphenol | HCID 7267 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 1-Bromo-3,7-dimethyloctane | HCID 137914 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 22641248 | HCID 22641248 | 70% |
Reaction Steps
Into a 500 ml four-necked flask was placed 36.7 g (0.3 mol) of 2,5-dimethylphenol, then, 73.0 g (0.33 mol) of 3,7-dimethyloctyl bromide was added, further, 150 g of water and 2.0 g (6.2 mmol) of tetrabutylammonium bromide were charged into the flask, and sufficient nitrogen purge was conducted by bubbling nitrogen through the mixture while stirring. Into this mixed solution was added an aqueous solution of sodium hydroxide (a solution prepared by dissolving 14.4 g (0.36 mol) of sodium hydroxide in 22 g of water) dropwise over 10 minutes while stirring. The mixture was heated to 95° C. and reacted for 30 minutes. Then, the mixture was kept at 100° C. and stirred for 4 hours to complete the reaction. The mixture was cooled to room temperature, and 200 ml of toluene was added before liquid separation. The intended substance was extracted into the organic layer which was washed with 200 ml of a 5% sodium hydroxide aqueous solution. The organic layer was dried over sodium sulfate, then, the solvent was distilled off by an evaporator. The intended 1-(3,7-dimethyloctyloxy)-2,5-dimethylbenzene was obtained from the condensed solution by distillation isolation (101 to 108° C./0.01 mmHg). The yield amount was 54.8 g (0.21 mol) and the yield was 70%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06818733B2 |
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| Source dataset | uspto-grants-2004_11 |
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| ORD ID | ord-e8c47552833542f7b55f53907c8857b0 |
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| Source note | uspto-grants-2004_11 |
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