Sulfur → Ethyl (7-methoxynaphthalen-1-yl)acetate
Reaction equation
[S].[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6][CH:5]=1>C(OCC)(=O)C>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([O:3][CH3:2])[CH:13]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 215 °C
Procedure
17.6 g sulfur and 90 g ethyl (7-methoxy-1,2,3,4-tetrahydro-1-naphthalenyl)-acetate were added into the reaction flask and heated to 215° C. with stirring. The reaction was carried out for 10 hours. After completion of the reaction, the reaction system was cooled to 60° C. 500 ml ethyl acetate was added and the mixture was stirred for 30 minutes. The mixture was filtered and the filter cake was washed with 100 ml ethyl acetate. Then, the filtrate was combined and vacuum evaporated to obtain 92 g brown oil with 82.4% content (HPLC). The yield is 85%.
Workup
- customAfter completion of the reaction
- temperaturethe reaction system was cooled to 60° C
- stirringthe mixture was stirred for 30 minutes
- filtrationThe mixture was filtered
- washthe filter cake was washed with 100 ml ethyl acetate
- customvacuum evaporated
Sources & evidence
- ORD record
- ord-22f87d6074434fb8a5dfa7cbb684a6ce
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029420B2
Reaction notes
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