Sodium Hydroxide → 2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

HRID 219810ノート

反応式

HRID 219810 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+]>CCO.O>[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 2

HCID 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 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A solution of methyl 2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylate (40 g; 147.97 mmol; 1 eq.) in EtOH (1 200 mL) at RT was treated with NaOH (88.78 mL; 5 M; 443.90 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for 1 hour. The reaction mixture was cooled to RT and concentrated to give a yellow solid which was taken up in water (800 mL) and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with HCl cc (40 mL) to pH 2 and it was extracted with EtOAc (2×400 mL). The combined organics were washed with brine, dried over MgSO4 and concentrated affording the title compound as a yellow solid (35.1 g, 92%). 1H NMR (DMSO-d6, 300 MHz) 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). LC/MS (Method B): 255.2 (M−H)−. HPLC (Method A) Rt 4.52 min (Purity: 96.4%).

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated
  3. customto give a yellow solid which
  4. washthe aqueous phase was washed twice with EtOAc
  5. extractionwas extracted with EtOAc (2×400 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-edd6be00122c438eb77c3989a2222b8e
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

反応ノート

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