Oxalic Acid → HCID 13592053, compound
Reaction equation
C(OC([O:6][C:7]1[C:8]([CH3:18])=[C:9]([CH3:17])[C:10]2[O:14][CH2:13][S:12][C:11]=2[C:15]=1[CH3:16])C)C.C(O)(=O)C(O)=O>C(Cl)Cl>[OH:6][C:7]1[C:8]([CH3:18])=[C:9]([CH3:17])[C:10]2[O:14][CH2:13][S:12][C:11]=2[C:15]=1[CH3:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5.0 g of 5-(1-ethoxyethoxy)-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Example 63) were dissolved in 20 ml of methylene chloride, and 10 g of silica gel-60 (a product of Merck and Co., Inc.) and 1 ml of a 10% w/v aqueous solution of oxalic acid were added. The mixture was then reacted for 1.5 hours at room temperature, after which the silica gel was filtered off. The methylene chloride was then distilled from the solution to yield a crude product, which was extracted with benzene. The extract was dried over anhydrous sodium sulfate, and the benzene was distilled off to yield crude crystals, which were recrystallized from an approximately 10:1 by volume mixture of benzene and petroleum ether, to yield 2.8 g of the title compound, melting at 131°-132° C.
Workup
- customThe mixture was then reacted for 1.5 hours at room temperature
- filtrationafter which the silica gel was filtered off
- distillationThe methylene chloride was then distilled from the solution
- customto yield a crude product, which
- extractionwas extracted with benzene
- dry with materialThe extract was dried over anhydrous sodium sulfate
- distillationthe benzene was distilled off
- customto yield crude crystals, which
- customwere recrystallized from an approximately 10:1 by volume mixture of benzene and petroleum ether
Sources & evidence
- ORD record
- ord-0fc42d380b5b42b3ac820169b0648cb7
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04871762
Reaction notes
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