Synthesis of model compounds for coal liquefaction research. Quarterly report No. 1, June 21, 1990--September 20, 1990
The objectives of this project are to develop feasible synthetic routes to produce (1) 4(4`-hydroxy-5`,6`,7`,8`-tetrahydro-l`-naphthylmethyl )- 6-methyldibenzothiophene, and (2) a 1-hydroxynaphthalene-benzothiophene polymer. Our experimental work during this quarter concentrated on. As several possible synthetic routes to the target molecule, 4(4`-hydroxy-5`,6`,7`,8`-tetrahydro- l`-naphthylmethyl )-6-methyldibenzothiophene. We tried synthesizing the intermediates for our first method, in which we couple a metalated 4-methyldibenzothiophene with 4-formyl-5,6,7,8-tetrahydro-1-naphthol. We found that we could easily metalate dibenzothiophene, and then add a methyl group to the 4-position to give 4-methyldibenzothiophene in greater than 80% yield by using t-butyllithium in tetrahydropyran followed by dimethylsulfate. However, adding the second metal to the desired 4` position using the same method was more difficult, and instead the reaction occurred on the methyl group. Therefore, we will investigate an alternative method, in which a hydroxy group is added in order to help direct the second metalation step to the 4` position on 4-methyldibenzothiophene.
- Research Organization:
- SRI International, Menlo Park, CA (United States)
- Sponsoring Organization:
- USDOE, Washington, DC (United States)
- DOE Contract Number:
- AC22-90PC90036
- OSTI ID:
- 10164773
- Report Number(s):
- DOE/PC/90036-T4; ON: DE92018412
- Resource Relation:
- Other Information: PBD: 2 Nov 1990
- Country of Publication:
- United States
- Language:
- English
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