Diethyl Ether → HCID 14851249, compound

HRID 359599Notes

Reaction equation

HRID 359599 reaction equation
[Cl:1][C:2]1[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:11]([S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Na+].C(OCC)C>C(O)C>[Cl:1][C:2]1[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:11]([S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])[CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 14851244HCID 14851244, compound

Product 1

HCID 14851249HCID 14851249, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 11.3 g (0.03 mole) of the ethyl 2-chloro-3-(2-methoxyethoxy)-4-ethylsulfonylbenzoate in 100 ml of 96% ethanol was added dropwise 16 ml (1.2 eq) of 10% sodium hydroxide. After stirring at room temperature for 4 hours, 100 ml of diethyl ether was added and the organic phase was extracted with 50 ml of 5% NaOH. The aqueous phase was acidified with 10% HCl and extracted two times with 50 ml chloroform. The organic phase was dried with MgSO4 and concentrated under vacuum to yield 8.8 grams of 2-chloro-3-(2-methoxyethoxy)4-ethylsulfonylbenzoic acid as a viscous oil.

Workup

  1. extractionthe organic phase was extracted with 50 ml of 5% NaOH
  2. extractionextracted two times with 50 ml chloroform
  3. dry with materialThe organic phase was dried with MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-12da1570047242cf946b1e1e13e2aa39
Source dataset
uspto-grants-1991_03
Patent number
US05001256

Reaction notes

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