Methanol → 2-(4-Cyclopropylphenyl)acetic acid

HRID 1913422노트

반응식

HRID 1913422 반응식
C[O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.CO.[OH-].[Na+]>C1COCC1>[CH:11]1([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:14])=[O:2])=[CH:6][CH:7]=2)[CH2:12][CH2:13]1

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66845395Methyl(4-cyclopropylphenyl)acetate

생성물 1

HCID 204905282-(4-Cyclopropylphenyl)acetic acid수율 60.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methyl(4-cyclopropylphenyl)acetate (710 mg, 3.73 mmol) was dissolved in 5 mL THF, 5 mL MeOH, and aqueous 1N NaOH (7.46 mmol) and the resulting mixture was heated at 45° C. overnight. After cooling to ambient temperature, the reaction was concentrated in vacuo and the residue was diluted with water (50 mL). The aqueous material was acidified with 1N HCl to pH˜3. A light brown precipitate formed which was collected by filtration and dried in a vacuum oven for 3 days to give (4-cyclopropylphenyl)acetic acid (SM-1ag, 395 mg, 60%). MS (ES−) 175.2 (M−H). 1H NMR (DMSO-d6) δ 0.57-0.61 (m, 2H), 0.86-0.91 (m, 2H), 1.81-1.88 (m, 1H), 3.45 (s, 2H), 6.97 (d, 2H), 7.08 (d, 2H), 12.20 (br s, 1H).

후처리

  1. concentrationthe reaction was concentrated in vacuo
  2. additionthe residue was diluted with water (50 mL)
  3. customA light brown precipitate formed which
  4. filtrationwas collected by filtration
  5. customdried in a vacuum oven for 3 days

출처 및 근거

ORD 기록
ord-c04158598db546e0a6dd933494e36fb3
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609680B2

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