Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,4-Butanediol | HCID 8064 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | Toluene-4-sulfonic acid, 2-benzyloxy-1-methylethyl ester | HCID 562182 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HO(CH2)4OCH(CH3)CH2OCH2Ph | HCID 85802961 | 58.3% |
Reaction Steps
HO(CH2)4OH (37 g), potassium hydroxide (23 g) and dioxane (200 ml) were charged into a four necked flask and heated to an internal temperature of 102° C. to dissolve potassium hydroxide. A solution of TsOCH(CH3)CH2OCH2Ph (63.7 g) obtained in Example 2-1 in dioxane (65 ml), was dropwise added over a period of 1 hour and stirred for 4 hours. The mixture was left to cool, then added to water (350 ml) and extracted three times with dichloromethane (100 ml). The organic layer was washed with water (20 ml). It was dried over magnesium sulfate, filtered and then concentrated by an evaporator to obtain a crude product (52 g). It was purified by silica gel column chromatography to obtain the above-identified compound (27.6 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06956138B2 |
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| Source dataset | uspto-grants-2005_10 |
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| ORD ID | ord-c9b22c7228584d37a66569033be51af3 |
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| Source note | uspto-grants-2005_10 |
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