Chlorobenzene → 5-CHLORO-1-TETRALONE
Reaction equation
[C:1]1(=[O:6])O[CH:2]1[CH2:3][CH3:4].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[Cl:11][C:12]1[CH:17]=[CH:4][CH:3]=[C:2]2[C:13]=1[CH2:14][CH2:15][CH2:16][C:1]2=[O:6]Participants
4
Procedure
Reaction of alpha-butyrolactone with chlorobenzene in the presence of aluminum chloride, as described in U.S. Pat. No. 3,657,400, produced 5-chloro-3,4-dihydro-1(2H)-naphthalenone. The latter was formylated with a combination of phosphorous oxychloride and dimethylformamide, yielding 1,5-dichloro-3,4-dihydronaphthalen-2-carboxaldehyde; mp 83.5°-84°, which was then reacted with ethyl thioglycolate and triethylamine in pyridine, as described in J.C.S. Perkin I, 2956 (1973), to produce ethyl 6-chloro-4,5-dihydronaphtho[1,2-b]thiophen-1-carboxylate; mp 81°-82°.
Sources & evidence
- ORD record
- ord-3d8e7854fc8c49529ddb1ccfda71a2a1
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04487778
Reaction notes
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