Potassium Hydroxide → HCID 5205498, compound

HRID 362762Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[OH-:15].[K+]>C(O)CCC>[CH2:2]([O:15][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 40 °C

Procedure

11-bromoundecanoic acid (2 g, 17.5 mmol) was added to a solution of potassium hydroxide (1.7 g, 30.2 mmol) in 1-butanol (20 mL) and the solution was stirred at 40° C. for 5 hrs. After cooling, the reaction mixture was extracted with ethyl acetate and water at pH=2. The organic phase was then washed with saturated sodium chloride, dried over sodium sulfate, and the solvent was removed under reduced pressure. The product was purified over silica column chromatography in 2-10% ethyl acetate/hexane/0.2% formic acid to yield 11-(1-butoxy)undecanoic acid (336 mg, 17%). mp 29°-30.5° C.; 1H NMR (300 MHz, CDCl3) δ 0.84-0.96 (t, 3H, J=7.3, CH3), 1.18-1.46 (bm, 14H, methylene envelope), 1.47-1.68 (bm, 6H, CH2CH2OCH2CH2, CH2CH2COOH), 2.31 (t, 2H, CH2COOH), 3.32-3.46 (bm, 4H, CH2OCH2), 11.02 (br, 1H, COOH); 13C NMR (75.4 MHz, CDCl3 δ 14.02, 19.43, 24.74, 26.21, 29.11, 29.28, 29.35, 29.56, 29.64, 29.76, 31.85, 34.14, 70.63, 70.94, 179.82; m/z 259 (M+H).

Workup

temperatureAfter cooling
extractionthe reaction mixture was extracted with ethyl acetate and water at pH=2
washThe organic phase was then washed with saturated sodium chloride
dry with materialdried over sodium sulfate
customthe solvent was removed under reduced pressure
customThe product was purified over silica column chromatography in 2-10% ethyl acetate/hexane/0.2% formic acid

Sources & evidence

ORD record: ord-1846afc8fdb0436089e1e2cc974836f1
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05871954

Reaction notes

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