Sodium Hydroxide → 3-Methyl-4-[2-(trifluoromethyl)phenyl]benzoic acid

HRID 219774

反応式

HRID 219774 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19].[OH-].[Na+]>CCO.O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:19])([F:20])[F:21]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 59606539Methyl 2-methyl-2'-(trifluoromethyl)biphenyl-4-carboxylate

生成物 1

HCID 219478123-Methyl-4-[2-(trifluoromethyl)phenyl]benzoic acid収率 84%

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

To a solution of methyl 2-methyl-2′-(trifluoromethyl)biphenyl-4-carboxylate, prepared in step 1 (3 g; 10.19 mmol; 1 eq.) in EtOH (90 mL), was added at RT an aqueous solution of sodium hydroxide (6.12 mL; 5 M; 30.58 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for one hour. The reaction mixture was concentrated under vacuum to give a brown solid. It was taken up in water (400 mL) and the aqueous phase was washed twice with EtOAc (200 mL). Aqueous phase was acidified with concentrated HCl (2 mL) to pH 2. Then it was concentrated under vacuum until a precipitate was formed (⅓ of volume). The suspension was filtered off and dried under vacuum, affording the title compound as a beige solid (2.41 g, 84%). 1H NMR: (DMSO-d6, 300 MHz) δ 13.03 (s, 1H), 7.91-7.68 (m, 5H), 7.38-7.36 (d, J=8.27 Hz, 1H), 7.27-7.25 (d, J=8.24 Hz, 1H), 2.05 (s, 3H). LC/MS (Method A): 279.0 (M−H)−. HPLC (Method A) Rt 4.49 min (Purity: 95.7%).

後処理

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto give a brown solid
  3. washthe aqueous phase was washed twice with EtOAc (200 mL)
  4. concentrationThen it was concentrated under vacuum until a precipitate
  5. customwas formed (⅓ of volume)
  6. filtrationThe suspension was filtered off
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-50b1b3cf03a945c0a25f99461b0a7743
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

関連ノート

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