Methanol → 2-(4-Cyclopropylphenyl)acetic acid

HRID 1913422ノート

反応式

HRID 1913422 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 204905282-(4-Cyclopropylphenyl)acetic acid収率 60.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c04158598db546e0a6dd933494e36fb3
出典データセット
uspto-grants-2013_12
特許番号
US08609680B2

反応ノート

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