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Potassium Iodide → Ethyl 2-[4-(acetyloxy)-2-methylphenoxy]-2-methylpropanoate

HRID 9627
Notes
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Reaction equation

HRID 9627 reaction equation
C([C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([CH3:19])[CH:5]=1)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.ClC1C=CC=[C:34]([C:38]([O:40]O)=[O:39])C=1.[I-].[K+]>ClCCl>[C:38]([O:40][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:15])([CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([CH3:19])[CH:5]=1)(=[O:39])[CH3:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6101p-Toluenesulfonic acidHCID 70297m-Chloroperbenzoic acidHCID 16756777Ethyl 2-(4-acetyl-2-methylphenoxy)-2-methylpropanoate2×

Product 1

HCID 21986549Ethyl 2-[4-(acetyloxy)-2-methylphenoxy]-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Conditions

Temperature
40 °C

Procedure

A solution of ethyl 2-(4-acetyl-2-methylphenoxy)-2-methylpropanoate (intermediate 8, 37.33 g) in dichloromethane (650 ml) was treated with 4-toluenesulphonic acid (2.75 g) followed by m-chloroperbenzoic acid (60.5 g) and the mixture warmed to 40° C. and stirred under nitrogen for 19 hours. The cooled mixture was treated with dichloromethane (350 ml) and the resulting mixture added to aqueous potassium iodide (1000 ml, 10% solution). The organic layer was collected and washed twice with water and brine, then dried over sodium sulfate, filtered and the filtrate concentrated to give the title compound as an orange oil.

Workup

  1. customThe organic layer was collected
  2. washwashed twice with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-ac4f6997785540cfabd1e40607d0df66
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091237B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes