Diethyl Ether → HCID 14851228, compound

HRID 1032238Notes

Reaction equation

HRID 1032238 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)-4ethylsulfonylbenzoate 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 1 N 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-methoxyethoxy)-4-ethylsulfonylbenzoic acid as a viscous oil.

Workup

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

Sources & evidence

ORD record
ord-26aaca48bf4048ba973afb05b42c8845
Source dataset
uspto-grants-1990_09
Patent number
US04957538

Reaction notes

Loading…