Potassium Hydroxide → 2,2,14,14-Tetramethyl-8-oxopentadecanedioic acid

HRID 1159715노트

반응식

HRID 1159715 반응식
[OH-].[K+].C([O:5][C:6](=[O:30])[C:7]([CH3:29])([CH3:28])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:26])([CH3:25])[C:20]([O:22]CC)=[O:21])C>O.C(O)C>[O:27]=[C:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:26])([CH3:25])[C:20]([OH:22])=[O:21])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]([CH3:29])([CH3:28])[C:6]([OH:30])=[O:5]

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 112232782,2,14,14-Tetramethyl-8-oxopentadecanedioic acid diethyl ester

생성물 1

HCID 113368222,2,14,14-Tetramethyl-8-oxopentadecanedioic acid수율 79%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

A solution of KOH (25 g) in water (50 mL) was added to a solution of 2,2,14,14-tetramethyl-8-oxo-pentadecanedioic acid diethyl ester (10.69 g, 155 mmol) in ethanol (400 mL), then heated at reflux for 4 h. After cooling, the solution was evaporated to a volume of ca. 50 mL and diluted with water (800 mL). The organic impurities were removed by extracting with dichloromethane (2×200 mL). The aqueous layer was acidified to pH 2 with concentrated hydrochloric acid (50 mL) and extracted with methyl tert.-butyl ether (MTBE, 3×200 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to give the crude product (9.51 g) as an oil. Crystallization from hexanes/MTBE (50 mL:25 mL) afforded 8-oxo-2,2,14,14-tetramethylpentadecanedioic acid (6.92 g, 79%) as waxy, white crystals. M.p.: 83-84° C. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 12.03 (s, 2 H), 2.37 (t, 4 H, J=7.3 Hz), 1.52-1.34 (m, 8 H), 1.28-1.10 (m, 8 H), 1.06 (s, 12 H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 210.5, 178.8, 41.7, 41.2, 29.1, 25.0, 24.4, 23.1. HRMS (LSIMS, gly): Calcd. for C19H35O5 (MH+): 343.2484, found: 343.2485.

후처리

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. temperatureAfter cooling
  4. customthe solution was evaporated to a volume of ca. 50 mL
  5. additiondiluted with water (800 mL)
  6. customThe organic impurities were removed
  7. extractionby extracting with dichloromethane (2×200 mL)
  8. extractionextracted with methyl tert.-butyl ether (MTBE, 3×200 mL)
  9. dry with materialThe combined organic layers were dried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customto give the crude product (9.51 g) as an oil
  12. customCrystallization from hexanes/MTBE (50 mL:25 mL)

출처 및 근거

ORD 기록
ord-7f0eb7589bae478f96b0d35a348977f0
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812199B2

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