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

HRID 1909572

반응식

HRID 1909572 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-d315281a4d34408083b84a4ca9efe36d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598374B2

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