Hydrochloric Acid → 2-(4-(Trifluoromethyl)phenyl)propanoic acid

HRID 1464194

反応式

HRID 1464194 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH3:15])[C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15062351Ethyl 2-(4-(trifluoromethyl)phenyl)propanoate

生成物 1

HCID 102424842-(4-(Trifluoromethyl)phenyl)propanoic acid収率 52.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1.93 g (7.8 mmol) of ethyl 2-(4-[trifluoromethyl]phenyl)propionate, 10 mL of 1N NaOH, and 10 mL of absolute ethanol was heated to reflux for 3 hours, allowed to cool to room temperature, and poured into 50 mL of 1N HCl. The resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded an oil which was crystallized from hexanes to give 0.90 g (50% yield) of the acid as a white, crystalline solid: mp 56°-58° C.; 1H NMR (CDCl3) 1.47 (d, 3H, J=7 Hz), 3.73 (q, 1H, J=7 Hz), 7.36 (d, 2H, J=8 Hz), 7.52 (d, 2H, J=8 Hz); 19F NMR (CDCl3, relative to CFCl3)-63.2 ppm (s); IR (neat) 2963, 1712, 1619, 1419, 1327, 1264, 1232, 1166, 1124, 1072, 1019, 843 cm-1.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. extractionThe resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane
  4. dry with materialCombination, drying (MgSO4), and concentration of the organic layers
  5. customafforded an oil which
  6. customwas crystallized from hexanes

出典と根拠

ORDレコード
ord-e93fe74613294760b335087328a20cb5
出典データセット
uspto-grants-1994_04
特許番号
US05302752

関連ノート

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