Nitrogen → 1-(tert-Butoxy)naphthalene
Reaction equation
[CH2:1]=[C:2]([CH3:4])[CH3:3].C(O)CCCCC.[C:12]1([OH:22])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.N#N>>[C:2]([O:22][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:1]Participants
5
Procedure
In a 200 ml autoclave, 300 mmol of isobutene, 50 mmol of 1-hexanol, 50 mmol of 1-naphthol and 300 mg of tin oxide/silicon dioxide/methylsilicon sesquioxide glass of composition 3 SnO2 : 97 SiO2 : 0 MeSiO1.5 were stirred at a pressure of 40 bar N2 and at a temperature of 140° C. for 16 h. Analysis of the product mixture by gas chromatography gave a yield of 1-naphthyl tert-butyl ether of 39.5% (based on 1-naphthol) as compared to a yield of 1-hexyl tert-butyl ether of 63.6% (based on 1-hexanol). In an analogous way, when the catalyst 1.5 Al2O3 : 97 SiO2 : 0 MeSiO1.5 was used, a yield of 1-naphthyl tert-butyl ether of 67.6% and a yield of 1-hexyl tert-butyl ether of 37.4% were achieved.
Sources & evidence
- ORD record
- ord-be66525c586540e9908f78835301eabc
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06121187
Reaction notes
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