Water → 2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

HRID 400742ノート

反応式

HRID 400742 の反応式
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([O:12]C)=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].[OH-].[Na+].O>CCO>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 58554139Methyl 2-(methoxymethyl)-2'-methyl-[1,1'-biphenyl]-4-carboxylate

生成物 1

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid収率 92.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of methyl 2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylate obtained in step 3 (40 g; 147.97 mmol) in EtOH (1200 mL) was added NaOH (88.78 mL; 5 M; 443.90 mmol) after which the mixture was heated at 60° C. for one hour. Reaction mixture was cooled to room temperature and concentrated under vacuum to give a yellow solid. Water was added and the aqueous phase was washed with EtOAc. The aqueous phase was then acidified with HCl (1 M) and extracted with EtOAc to give the title compound as a yellow solid (35.1 g, 92%). 1H NMR (DMSO-d6) δ 12.99 (br s, 1H), 8.09 (s, 1H), 7.92-7.89 (m, 1H), 7.33-7.22 (m, 4H), 7.10-7.08 (m, 1H), 4.11 (m, 2H), 3.18 (s, 3H), 1.99 (s, 3H). HPLC (Method A) Rt 4.52 min (Purity: 96.4%). LC/MS (Method B): 255.2 (M−H)−.

後処理

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. concentrationconcentrated under vacuum
  4. customto give a yellow solid
  5. washthe aqueous phase was washed with EtOAc
  6. extractionextracted with EtOAc

出典と根拠

ORDレコード
ord-6395ceaf6725416c83ae6143f3a7a53d
出典データセット
uspto-grants-2014_06
特許番号
US08741923B2

反応ノート

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