Diethyl Ether → HCID 14851228, compound

HRID 1494678Notes

Reaction equation

HRID 1494678 reaction equation
[Br: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+].CCOCC>CO.O>[Br: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 14851225HCID 14851225, compound

Product 1

HCID 14851228HCID 14851228, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To 7.26 g (0.02 mole) of the ethyl 2-bromo-3-(2-methoxyethoxy)-4-ethylsulfonylbenzoate in 50 ml of 80% methanol/water was added 1.2 g (0.03 mole) of sodium hydroxide. After stirring at room temperature overnight, 100 ml of ether was added and the organic phase was extracted three times with 50 ml of 1N NaOH. The combined base extracts were acidified and extracted three times with methylene chloride. The methylene chloride was dried and concentrated to yield 6.6 grams of 2-bromo-3-(2-methoxy-ethoxy)-4-ethylsulfonylbenzoic acid as a viscous oil.

Workup

  1. extractionthe organic phase was extracted three times with 50 ml of 1N NaOH
  2. extractionextracted three times with methylene chloride
  3. dry with materialThe methylene chloride was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e9ffb4ae7174012bece74ec1348d197
Source dataset
uspto-grants-1991_06
Patent number
US05026896

Reaction notes

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