m-Chloroperbenzoic acid → Ethyl 2-(4-acetoxy-2-methylphenoxy)acetate

HRID 445857

反応式

HRID 445857 の反応式
C([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([CH3:17])[CH:5]=1)(=O)C.C1C=C(Cl)C=[C:20]([C:25]([O:27]O)=[O:26])C=1>ClCCl>[C:25]([O:27][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([CH3:17])[CH:5]=1)(=[O:26])[CH3:20]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 21986544Ethyl 2-(4-acetyl-2-methylphenoxy)acetate

生成物 1

HCID 21986316Ethyl 2-(4-acetoxy-2-methylphenoxy)acetate収率 72%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of ethyl 2-(4-acetyl-2-methylphenoxy)acetate (683) (8.78 g, 37 mmol), mCPBA (2.eq.), and p-TsOH monohydrate (0.15 eq.) in dichloromethane (160 mL) was heated at 40° C. overnight. The reaction was cooled to room temperature and washed with 1M KI (2×200 mL), 5% NaHSO3 (2×150 mL), and water (200 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to provide ethyl 2-(4-acetoxy-2-methylphenoxy)acetate (684) (72%).

後処理

  1. washwashed with 1M KI (2×200 mL), 5% NaHSO3 (2×150 mL), and water (200 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-f11a86ffbbe04e5f990c3155298a406d
出典データセット
uspto-grants-2013_07
特許番号
US08476308B2

関連ノート

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