Trifluoroacetic acid → Oxacyclotridecan-2-one
Reaction equation
[C:1]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=[O:17]>>[C:1]1(=[O:13])[O:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1Participants
3
Procedure
Cyclododecanone was treated with trifluoroacetic acid to form the lactone (Huisgen, R. et al., ibid), dodecanolid (yield 75%; bp 111°-115° C. at 8 mm). The lactone was hydrolyzed to form 12-hydroxydodecanoic acid (Smissman, E. et al., ibid) (yield 92%; mp 82°-4° C.). The hydroxy acid was converted to 12-bromododecanoic acid (VI) with 48% HBr in the presence of H2SO4 (Jocelyn, P. et al., ibid) (yield 88%; mp 52°-55° C.).
Sources & evidence
- ORD record
- ord-c1cc0b085e674433814df35b1351cfb3
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04845271
Reaction notes
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