Sodium Hydroxide → 2-(4-Bromophenyl)-2-methylpropanoic acid

HRID 218222Notes

Reaction equation

HRID 218222 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:15])([CH3:14])[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:15])([CH3:14])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11277257Ethyl 2-(4-bromophenyl)-2-methylpropanoate

Product 1

HCID 109336792-(4-Bromophenyl)-2-methylpropanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 22A (3.7 g, 13.6 mmoles) in tetrahydrofuran (110.0 ml) and methanol (37.0 ml) was added 2 N sodium hydroxide (19.0 ml) and the solution was stirred at ambient temperature for about 16 hours. The reaction mixture was concentrated in vacuum down to the water layer, was cooled with an ice bath, and was acidified by addition of 2N hydrochloric acid. The precipitate was filtered off and was dried in vacuum to provide the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum down to the water layer
  2. temperaturewas cooled with an ice bath
  3. additionwas acidified by addition of 2N hydrochloric acid
  4. filtrationThe precipitate was filtered off
  5. customwas dried in vacuum

Sources & evidence

ORD record
ord-e4fab534b8164ed0aefc0af450add9b5
Source dataset
uspto-grants-2012_06
Patent number
US08198331B2

Reaction notes

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