Trifluoroacetic acid → Oxacyclotridecan-2-one

HRID 231349

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]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 13246Cyclododecanone

Product 1

HCID 70354Oxacyclotridecan-2-oneYield 75%

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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845271

Linked notes

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