Synthesis of model compounds for coal liquefaction research

Technical Report · Fri Nov 02 04:00:00 EST 1990

DOI:https://doi.org/10.2172/7113040· OSTI ID:7113040

Hirschon, A S; Asaro, M; Bottaro, J

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: DOE; USDOE, Washington, DC (United States)
• DOE Contract Number: AC22-90PC90036
• OSTI ID: 7113040
• Report Number(s): DOE/PC/90036-T4; ON: DE92018412
• Country of Publication: United States
• Language: English

Related Subjects

01 COAL, LIGNITE, AND PEAT
010405* -- Coal
Lignite
& Peat-- Hydrogenation & Liquefaction
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201 -- Chemical & Physicochemical Properties
CHEMICAL PREPARATION
CHEMICAL REACTIONS
COAL LIQUIDS
DESULFURIZATION
DOCUMENT TYPES
FLUIDS
HETEROCYCLIC COMPOUNDS
LIQUIDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
POLYCYCLIC SULFUR HETEROCYCLES
PROGRESS REPORT
SYNTHESIS