Water → 10-Propoxydecanoic acid

HRID 619762Notes

Reaction equation

HRID 619762 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[OH-].[K+].O.[CH2:17]([OH:20])[CH2:18][CH3:19]>>[CH2:17]([O:20][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:18][CH3:19]

Participants

5

Reactant 4

HCID 962WaterHCID 10311-PropanolHCID 14797Potassium HydroxideHCID 14271210-Bromodecanoic Acid

Product 1

HCID 12209810-Propoxydecanoic acidYield 12%

Conditions

Temperature
102 °C

Procedure

10-bromodecanoic acid (1g, 3.98 mmol) was added to a solution of potassium hydroxide (0.893g, 15.9 mmol) in n-propanol (30 mL) and stirred at 102° C. for 18 hrs. The reaction was allowed to cool to room temperature after the addition of 20 mL water. After acidification to pH=1 and extraction into ethyl acetate, the organic phase was dried over sodium sulfate and solvent removed at reduced pressure to yield a yellow oil. The product was purified by silica column chromatography in 2% diethyl ether/methylene chloride/0.2% formic acid, and then in 7% ethyl acetate/hexane/0.3% formic acid. Recrystallization from hexane at -20° C. yielded 10-(propoxy)decanoic acid (74 mg, 12%): mp <30° C.; 1H NMR (300 MHz, CDCl3) δ0.91 (t, 3H, J=7.5, CH3), 1.18-1.40 (br, 10H, methylene envelope), 1.48-1.67 (bm, 6H, CH3CH2CH2OCH2CH2, CH2CH2COOH), 2.33 (t, 2H, J=7.4, CH2COOH), 3.31-3.45 (bm, 4H, CH2OCH2), 10.37 (br, 1H COOH); 13C NMR (75.4 MHz, CDCl3) 10.67, 22.94, 24.72, 26.19, 29.09, 29.22, 29.41, 29.74, 34.11, 70.88, 72.53, 179.69; m/z 231 (M+H).

Workup

  1. temperatureto cool to room temperature
  2. extractionAfter acidification to pH=1 and extraction into ethyl acetate
  3. dry with materialthe organic phase was dried over sodium sulfate and solvent
  4. customremoved at reduced pressure
  5. customto yield a yellow oil
  6. customThe product was purified by silica column chromatography in 2% diethyl ether/methylene chloride/0.2% formic acid
  7. customRecrystallization from hexane at -20° C.

Sources & evidence

ORD record
ord-eb62db27eb734fcd8a394931ad84af6c
Source dataset
uspto-grants-1999_09
Patent number
US05959145

Reaction notes

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