Sodium Sulfite → HCID 18620089, compound

HRID 1862613Notes

Reaction equation

HRID 1862613 reaction equation
[CH2:1]([O:3][C:4]1[CH:16]=[C:15]([CH2:17][CH2:18][OH:19])[CH:14]=[CH:13][C:5]=1[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].[Cl:20]OC(C)(C)C.S([O-])([O-])=O.[Na+].[Na+]>ClCCl.O>[Cl:20][C:14]1[C:15]([CH2:17][CH2:18][OH:19])=[CH:16][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:13]=1)[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 3

HCID 24437Sodium SulfiteHCID 521297Tert-Butyl hypochloriteHCID 18620114HCID 18620114, compound

Product 1

HCID 18620089HCID 18620089, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 2-[2-ethoxy-4-(2-hydroxyethyl)phenoxy]acetate (1.15 g) in dichloromethane (4.3 ml) was added tert-butyl hypochlorite (478 μl) at room temperature, and the mixture was stirred for 15 minutes. To the reaction mixture was added a solution of sodium sulfite (542 mg) in water (5 ml), and the resulting mixture was stirred for 10 minutes at room temperature. The mixture was extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure gave ethyl 2-[5-chloro-2-ethoxy-4-(2-hydroxyethyl)phenoxy]acetate (1.28 g).

Workup

  1. stirringthe resulting mixture was stirred for 10 minutes at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-9573a91593d9428596c3812c88f6acff
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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