Sodium Hydroxide → 3-Cyclopentyl-2-phenylpropanoic acid

HRID 889599노트

반응식

HRID 889599 반응식
C[O:2][C:3](=[O:17])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>CO.O>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:3]([OH:17])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 462211553-Cyclopentyl-2-phenylpropionic acid methyl ester

생성물 1

HCID 186266423-Cyclopentyl-2-phenylpropanoic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To title A compound, 3-cyclopentyl-2-phenylpropionic methyl ester (13.0 g, 56 mmol) in 100 mL of methanol is added a solution of 5.6 g (140 mmol) of NaOH in 8 mL of water. The reaction mixture is stirred at ambient temperature overnight. The methanol is evaporated and the residue is dissolved in 200 mL of water and extracted with ethyl ether. The aqueous phase is separated and adjusted to pH 2-3 with 1 N HCl and extracted with MTBE twice. The combined extracts are washed with saturated sodium chloride and dried over anhydrous magnesium sulfate. The material is evaporated to a yellow oil that crystallizes to provide 3-cyclopentyl-2-phenylpropionic acid as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 1.7 (m, 2H), 2.1 (m, 2H), 2.2 (m, 3H), 2.4(m, 3H), 2.4 (m, 1H), 4.2 (t, J=7.7 Hz, 1H), 7.9 (m, 5H); LC/MS 236 (M+NH4+).

후처리

  1. customThe methanol is evaporated
  2. dissolutionthe residue is dissolved in 200 mL of water
  3. extractionextracted with ethyl ether
  4. customThe aqueous phase is separated
  5. extractionextracted with MTBE twice
  6. washThe combined extracts are washed with saturated sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe material is evaporated to a yellow oil
  9. customthat crystallizes

출처 및 근거

ORD 기록
ord-3bc574c6b9864c999325dc5e769e919f
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252931B2

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