Hydrochloric Acid → 2,2-Dimethylpentanoic acid

HRID 1252178

반응식

HRID 1252178 반응식
[C:1]([Li])(C)(C)[CH3:2].[CH:6](NC(C)C)(C)C.[CH3:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16].C(I)CC.Cl>CCCCC.O1CCCC1>[CH3:13][C:14]([CH3:6])([CH2:18][CH2:1][CH3:2])[C:15]([OH:17])=[O:16]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 6590Isobutyric AcidHCID 7912DiisopropylamineHCID 336431-IodopropaneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 144552,2-Dimethylpentanoic acid

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A 240 ml (285 mmol) portion of a solution of t-butyllithium in pentane (1.18M) was added dropwise to a solution of 42 ml (290 mmol) of diisopropylamine in 300 ml of dry tetrahydrofuran while it was stirred with -5° bath cooling under argon. A 12.7 ml (135 mmol) portion of 2-methylpropionic acid in 15 ml of dry tetrahydrofuran was then added dropwise to the reaction mixture. A 14.3 ml (140 mmol) portion of n-propyliodide was then added dropwise to the reaction mixture as stirring was continued with ice bath cooling. The resultant mixture was stirred two hours without cooling and then acidified by the slow addition of 10% hydrochloric acid. The resultant mixture was extracted several times with ether and the combined extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo to yield 16.3 g of 2,2-dimethylpentanoic acid, having the following spectral characteristics: nmr (CDCl3) δ 0.94 (3H, t, J=8.5 Hz), 1.20 (6H, s), 1.2-1.8 (4H, m) and 11.3 ppm (1H, broad s); ir (CHCl3) 860, 945, 1185, 1240, 1290, 1310, 1370, 1410, 1480, 1700 and 2400-3400 cm-1 (broad).

후처리

  1. temperaturecooling under argon
  2. stirringas stirring
  3. customwas continued with ice bath
  4. temperaturecooling
  5. temperaturewithout cooling
  6. extractionThe resultant mixture was extracted several times with ether
  7. washthe combined extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-30aefb1ccde8424baecf12e601fce89f
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04742080

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