Hydrochloric Acid → 2,3-Dimethyl-5-nitrobenzoic acid phenyl ester

HRID 1974554

反応式

HRID 1974554 の反応式
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(Cl)(=O)C(Cl)=O.[C:21]1([O-])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Na+].Cl>ClCCl.O1CCCC1.CN(C)C=O>[C:21]1([O:5][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=[C:10]([CH3:11])[C:2]=2[CH3:1])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 4445035Phenolate SodiumHCID 137581312,3-Dimethyl-5-nitrobenzoic acid

生成物 1

HCID 137581332,3-Dimethyl-5-nitrobenzoic acid phenyl ester収率 63.5%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2,3-dimethyl-5-nitrobenzoic acid (1.7 g) in dichloromethane (20 ml) was added oxalylchloride (1.0 ml) and dimethylformamide (0.05 ml). After the solution was stirred for 1 hour at room temperature, the solvent was removed in vacuo. The residue was dissolved in tetrahydrofuran (20 ml). To the solution was added a solution of sodium phenolate (20 mmol) in tetrahydrofuran (20 ml) at 0° C. The mixture was stirred for 30 minutes and poured into diluted hydrochloric acid (110 ml). The organic layer was extracted with ethyl acetate (50 ml) and washed with water (50 ml×3). The solution was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was purified by a column of silica gel to give a yellow solid of 2,3-dimethyl-5-nitrobenzoic acid phenyl ester (1.50 g).

後処理

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in tetrahydrofuran (20 ml)
  3. stirringThe mixture was stirred for 30 minutes
  4. extractionThe organic layer was extracted with ethyl acetate (50 ml)
  5. washwashed with water (50 ml×3)
  6. dry with materialThe solution was dried over magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by a column of silica gel

出典と根拠

ORDレコード
ord-a0f3c9383975483394770a7f1365aaf5
出典データセット
uspto-grants-1994_02
特許番号
US05283251

関連ノート

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