Methyl chloroformate → Benzoic Acid

HRID 2051608ノート

反応式

HRID 2051608 の反応式
COC(Cl)=O.C(O[C:11]1N=[C:18]([CH3:20])[C:17](Cl)=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])CCC.NCCC1C=CC(C(O)=O)=CC=1.[Na].C([O-])(=O)C.[Na+]>CC(C)=O.C(N(CC)CC)C>[C:13]([OH:15])(=[O:14])[C:12]1[CH:11]=[CH:20][CH:18]=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 6586Methyl chloroformateHCID 517045Sodium AcetateHCID 203792372-Butoxy-5-chloro-6-methyl-nicotinic acidHCID 705908304-(2-Aminoethyl)-benzoic acid sodium

生成物 1

HCID 243Benzoic Acid

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回HCID 8471Triethylamine溶媒

実験手順

2.8 g of triethylamine and 2.6 g of chloroformic acid methyl ester are added, while stirring and cooling with ice, to 6.1 g of 2-butoxy-5-chloro-6-methyl-nicotinic acid (melting point 95°-97° C., prepared by chlorinating 2-butoxy-6-methyl-nicotinic acid in dilute glacial acetic acid) in 75 ml of acetone. The mixture is stirred for a further 15 minutes and then added, while stirring, to 25 ml of a 1-molar solution of 4-(2-amino-ethyl)-benzoic acid-sodium, additionally containing 0.025 mol of sodium acetate and to which 25 ml of acetone has been added. Stirring of the mixture is continued for 2 hours at room temperature, the acetone is removed under reduced pressure, the remaining aqueous solution is acidified, the precipitated reaction product is filtered off with suction, reprecipitated from ammonia and recrystallized from dilute methanol or ethyl acetate. The 4-(2-<2-butoxy-5-chloro-6-methyl-nicotinamido>-ethyl)-benzoic acid obtained melts at 148°-150° C.

後処理

  1. stirringThe mixture is stirred for a further 15 minutes
  2. additionadded
  3. stirringStirring of the mixture
  4. customthe acetone is removed under reduced pressure
  5. customthe precipitated reaction product
  6. filtrationis filtered off with suction
  7. customreprecipitated from ammonia
  8. customrecrystallized from dilute methanol or ethyl acetate

出典と根拠

ORDレコード
ord-cce071f07ec347b98dd8c54d8dd9d893
出典データセット
uspto-grants-1980_01
特許番号
US04181658

反応ノート

読み込み中…