Lithium hydroxide, monohydrate → 2-Nitro-terephthalic acid 1-tert-butyl ester

HRID 1526031ノート

反応式

HRID 1526031 の反応式
C[O:2][C:3](=[O:20])[C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[C:6]([N+:17]([O-:19])=[O:18])[CH:5]=1.O.[OH-].[Li+]>C1COCC1.O>[C:11]([O:10][C:8](=[O:9])[C:7]1[CH:15]=[CH:16][C:4]([C:3]([OH:20])=[O:2])=[CH:5][C:6]=1[N+:17]([O-:19])=[O:18])([CH3:14])([CH3:12])[CH3:13]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 675127822-Nitro-terephthalic acid 1-tert-butyl ester 4-methyl ester

生成物 1

HCID 686717752-Nitro-terephthalic acid 1-tert-butyl ester収率 93%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2-Nitro-terephthalic acid 1-tert-butyl ester 4-methyl ester (21.49 mmol) was dissolved in THF (143 mL) and treated with lithium hydroxide monohydrate (1.35 g, 32.24 mmol) in water (97 mL). The reaction was stirred at room temperature for 2 hours then partially evaporated, cooled with an ice/water bath and treated with 1N HCl dropwise (35 mL). Precipitation of a solid occurred. The mixture was then extracted with DCM (150 mL and 2×50 mL) The aqueous phase was further treated with 1N HCl (10 mL) and extracted with DCM (2×50 mL). The combined organic layers were then washed with water and finally with brine. After drying over sodium sulphate and evaporation, 5.34 g of title compound were obtained as a reddish solid in 93% overall yield.

後処理

  1. customthen partially evaporated
  2. temperaturecooled with an ice/water bath
  3. additiontreated with 1N HCl dropwise (35 mL)
  4. customPrecipitation of a solid
  5. extractionThe mixture was then extracted with DCM (150 mL and 2×50 mL) The aqueous phase
  6. additionwas further treated with 1N HCl (10 mL)
  7. extractionextracted with DCM (2×50 mL)
  8. washThe combined organic layers were then washed with water and finally with brine
  9. dry with materialAfter drying over sodium sulphate and evaporation

出典と根拠

ORDレコード
ord-77c07ae75c874d7bae8703357784eea0
出典データセット
uspto-grants-2015_07
特許番号
US09085558B2

反応ノート

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