盐酸 → 2-Methyl-5(2-chloro-4-trifluoromethylphenoxy)-benzoic acid

HRID 358193笔记

反应方程式

HRID 358193 反应方程式
[H-].[Na+].O[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:13])[CH:5]=1.[Cl:14][C:15]1[CH:16]=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:18]=[CH:19][C:20]=1F.Cl.CN(C)C=[O:30]>O>[CH3:13][C:6]1[CH:5]=[CH:4][C:12]([O:30][C:20]2[CH:19]=[CH:18][C:17]([C:22]([F:25])([F:24])[F:23])=[CH:16][C:15]=2[Cl:14])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

参与物

7

反应物 5

HCID 313盐酸HCID 6228N,N-二甲基甲酰胺HCID 24758氢化钠HCID 684754-羟基-2-甲基苯甲酸HCID 1571533-氯-4-氟三氟甲苯

产物 1

HCID 212870662-Methyl-5(2-chloro-4-trifluoromethylphenoxy)-benzoic acid

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

A mixture of sodium hydride (2.3 g, 50% dispersion in mineral oil, prewashed with petroleum, b.p. 40°-60°) and 4-hydroxy-2-methylbenzoic acid (3.4 g) in dry N,N-dimethylformamide (30 ml) was stirred for thirty minutes, then treated with 3-chloro-4-fluorobenzotrifluoride (4.5 g). The mixture was heated at 130° for five hours, cooled, diluted with water, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The extracts were washed with water and brine, dried and evaporated. The residue was recrystallised from petroleum (b.p. 80°-100°) to give 2-methyl-5(2-chloro-4-trifluoromethylphenoxy)-benzoic acid (2.06 g, m.p. 113°). A suspension of this material (1.34 g) in thionyl chloride (5 ml) was heated under reflux for one hour and the excess reagent removed in vacuo. The residue was dissolved in acetonitrile and again evaporated to give crude acid chloride.

后处理

  1. temperatureThe mixture was heated at 130° for five hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water and brine
  5. customdried
  6. customevaporated
  7. customThe residue was recrystallised from petroleum (b.p. 80°-100°)

来源与证据

ORD记录
ord-3fd1f6e933434511a7e2005f8f96d4d9
来源数据集
uspto-grants-1984_08
专利号
US04465508

反应笔记

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