Methylparaben → 4-Phenethyloxybenzoic Acid Methyl Ester

HRID 970786ノート

反応式

HRID 970786 の反応式
[H-].[Na+].C1COCC1.[CH3:8][O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[CH2:19](Br)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O.CN(C)C=O>[CH3:8][O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][CH:12]=1

参加物

7

反応物 4

HCID 7456MethylparabenHCID 7666Phenethyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

生成物 1

HCID 120638344-Phenethyloxybenzoic Acid Methyl Ester収率 29.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

NaH (60%) (4.400 g, 120.0 mmol) was added to freshly distilled THF chilled to 0° C., followed by 4-hydroxybenzoic acid methyl ester 9 (15.215 g, 100.0 mmol). After H2 evolution ceased, dimethylformamide (DMF) (20 ml) was added clearing the cloudy solution followed by phenethyl bromide 8 (16.39 ml, 120.0 mmol), and the mixture was stirred at 80° C. for 24 hours. Upon cooling, the mixture was poured into H2O and extracted. The organic extracts were combined, washed, dried, and evaporated. The residue was purified by chromatography to give about 7.6 g of 4-phenethyloxybenzoic acid methyl ester 10.

後処理

  1. temperatureUpon cooling
  2. extractionextracted
  3. washwashed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-95b31d6f44ce49f48e31e078970f5722
出典データセット
uspto-grants-2007_12
特許番号
US07312230B2

反応ノート

読み込み中…