Sodium Hydroxide → 3-(4-broMophenyl)-2,2-diMethylpropanoic acid

HRID 361468Notes

Reaction equation

HRID 361468 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:12]([O:14]C)=[O:13])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([C:12]([OH:14])=[O:13])([CH3:11])[CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22503289Methyl 4-bromo-α,α-dimethylbenzenepropanoate

Product 1

HCID 211862823-(4-broMophenyl)-2,2-diMethylpropanoic acidYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-bromo-4-(2-methoxycarbonyl-2-methylpropyl)benzene (7.79g) was dissolved in methanol (60 ml) and 2M aqueous sodium hydroxide solution (30 ml) was added. The solution was heated to reflux for 2 hours then cooled. The volume was reduced to ~25 ml by evaporation and the residue extracted with ethyl acetate (15 ml) then acidified with 2M hydrochloric acid and re-extracted with ethyl acetate (3×25 ml). The combined organic extract of the acidified aqueous phase was dried (MgSO4) and evaporated to give 1-bromo-4-(2-carboxy-2-methylpropyl)benzene (6.1 g); 1H NMR (d6 -DMSO): 1.08 (s, 6 H), 2.78 (s, 2 H), 7.11 (m, 2 H), 7.46 (m, 2 H); mass spectrum (CI+) 256 (M+H)+.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 2 hours
  3. temperaturethen cooled
  4. customThe volume was reduced to ~25 ml by evaporation
  5. extractionthe residue extracted with ethyl acetate (15 ml)
  6. extractionre-extracted with ethyl acetate (3×25 ml)
  7. extractionThe combined organic extract of the acidified aqueous phase
  8. dry with materialwas dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-4d947400cfca4a09bf967e5923b2be35
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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