2-Chlorobenzaldehyde → 3-(2-Chlorophenyl)acrylic acid

HRID 15498

反応式

HRID 15498 の反応式
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O.C(OC(=O)C)(=O)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[CH:2][C:1]([OH:4])=[O:3]

参加物

6

反応物 4

HCID 69962-ChlorobenzaldehydeHCID 7918Acetic Anhydride2 回HCID 14798Sodium HydroxideHCID 517044Potassium Acetate

生成物 1

HCID 195673-(2-Chlorophenyl)acrylic acid

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
145 °C

実験手順

A mixture of 18.4 g (0.19 mol) of potassium acetate in 70.3 g (0.5 mol) 2-chlorobenzaldehyde is heated to 145° C. Next 76.5 g (0.75 mol) of acetic anhydride is added in 1 hour. After dosing of 0.50 mol of acetic anhydride the mixture became clear. The mixture is stirred at 145° C. during 18 hours. The hot reaction mixture is poured into a mixture of 670 g of 6.4 w/w % aqueous NaOH (1.1 mol, 2.1 eq based on 2-chlorobenzaldehyde) and 200 mL toluene at 80° C. The final pH was 7.4. After separation of the organic phase, the water layer is again extracted with 100 mL of toluene at 80° C. The combined water phases are acidified with 380 g of 25 w/w % H2SO4 to pH 4.6. Crystallization starts at pH 6.4. The mixture is cooled to 25° C. and the product is isolated by filtration, washed with 100 mL of water and dried (vacuo, 50° C.). 3-(2-chloro-phenyl)-acrylic acid was obtained as an off white solid (100.2 g, 0.55 mol, yield 55%).

後処理

  1. customAfter separation of the organic phase
  2. extractionthe water layer is again extracted with 100 mL of toluene at 80° C
  3. customCrystallization
  4. temperatureThe mixture is cooled to 25° C.
  5. customthe product is isolated by filtration
  6. washwashed with 100 mL of water
  7. customdried (vacuo, 50° C.)

出典と根拠

ORDレコード
ord-e862e1156e4a4a7796b47dac015c698e
出典データセット
uspto-grants-2010_06
特許番号
US07732621B2

関連ノート

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