Hydrochloric Acid → HCID 13020555, compound

HRID 1680817Notes

Reaction equation

HRID 1680817 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Br[CH:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([O:17]C)=[O:16].[OH-].[Na+].Cl>CO.O>[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([OH:17])=[O:16])=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 90154-MethoxyphenolHCID 14798Sodium HydroxideHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 13020555HCID 13020555, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The starting material is prepared as follows: To the solution of 1,032 g of sodium methoxide in 12,000 ml of methanol 2,361 g of 4-methoxyphenol are added while stirring under nitrogen at 40°. After 30 minutes 4,100 g of methyl α-bromophenylacetate are added during 10 minutes and the mixture is refluxed for 5 hours. It is combined with 14,000 ml of 2 N aqueous sodium hydroxide and refluxing is continued for an additional hour. The mixture is stirred at room temperature overnight, diluted with 14,000 ml of water at 65° and 3,000 ml of concentrated hydrochloric acid are added during 1 hour. Stirring is continued for 2 hours at room temperature, the precipitate formed is filtered off and washed 3 times with 4,000 ml of water, to yield the α-(4-methoxyphenoxy)-phenylacetic acid melting at 108°-110°.

Workup

  1. customThe starting material is prepared
  2. temperaturethe mixture is refluxed for 5 hours
  3. temperaturerefluxing
  4. waitis continued for an additional hour
  5. stirringThe mixture is stirred at room temperature overnight
  6. stirringStirring
  7. customthe precipitate formed
  8. filtrationis filtered off
  9. washwashed 3 times with 4,000 ml of water

Sources & evidence

ORD record
ord-00202815c41446ed86f4a89fd4ed3ea7
Source dataset
uspto-grants-1981_06
Patent number
US04276294

Reaction notes

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