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

HRID 1909572Notes

Reaction equation

HRID 1909572 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-d315281a4d34408083b84a4ca9efe36d
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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