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

HRID 1378358Notes

Reaction equation

HRID 1378358 reaction equation
C[O:2][C:3]([C:5]([CH3:15])([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)=[O:4].[OH-].[Na+]>CO>[C:3]([C:5]([CH3:15])([CH3:14])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([Br:13])=[CH:11][CH:12]=1)([OH:4])=[O:2]

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

4-(2-Methoxycarbonyl-2-methylpropyl)bromobenzene (7.79 g) 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 approximately 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 4-(2-carboxy-2-methylpropyl)bromobenzene (6.1 g); 1H NMR (d6 -DMSO): 1.08 (s, 6H), 2.78 (s, 2H), 7.11 (m, 2H), 7.46 (m, 2H); 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 approximately 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-3bcdd9e693074875944a646173f4eef2
Source dataset
uspto-grants-1997_09
Patent number
US05668137

Reaction notes

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