Methanol → HCID 18786137, compound

HRID 1107858Notes

Reaction equation

HRID 1107858 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][CH:5]([CH2:11][CH2:12][CH3:13])[C:6]([O:8]CC)=[O:7].CO.[OH-].[Na+]>O>[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][CH:5]([CH2:11][CH2:12][CH3:13])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18786120HCID 18786120, compound

Product 1

HCID 18786137HCID 18786137, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

26.5 g (188 mmol) of ethyl 2-(2-bromophenoxy)pentanoate, 50 ml of methanol, 21.1 g (528 mmol) of sodium hydroxide pellets and 3 ml of water are placed in 250 ml three-necked flask equipped with a reflux condenser. The mixture is heated at reflux for 3 hours and then cooled to room temperature and concentrated. 200 ml of water are added and extraction is carried out with 150 ml of petroleum ether. The aqueous phase is subsequently acidified by the addition of a hydrochloric acid solution and then extracted with 3×200 ml of chloroform. The combined organic phases are dried over magnesium sulphate, filtered and concentrated under vacuum to give 23.8 g (99% yield) of 2-(2-bromophenoxy)pentanoic acid--M.p.=63° C.

Workup

  1. customequipped with a reflux condenser
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 3 hours
  4. concentrationconcentrated
  5. addition200 ml of water are added
  6. extractionextraction
  7. additionThe aqueous phase is subsequently acidified by the addition of a hydrochloric acid solution
  8. extractionextracted with 3×200 ml of chloroform
  9. dry with materialThe combined organic phases are dried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5f0582bbdcbd43d091a51b190c41bd37
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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