Sulfuric Acid → Butanoic acid, 2-bromo-3-methyl-, 1,1-dimethylethyl ester

HRID 1856410Notes

Reaction equation

HRID 1856410 reaction equation
[Br:1][CH:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[CH3:9][C:10](=[CH2:12])[CH3:11].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>CCOCC>[Br:1][CH:2]([CH:6]([CH3:8])[CH3:7])[C:3]([O:5][C:10]([CH3:12])([CH3:11])[CH3:9])=[O:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 112682-Bromoisovaleric acidHCID 516892Sodium Bicarbonate

Product 1

HCID 13821159Butanoic acid, 2-bromo-3-methyl-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.0 mm of (+)-2-bromo-3-methylbutyric acid is dissolved in a solvent consisting of 100 ml of ether, 100 ml of isobutylene, and 0.5 ml of sulfuric acid. The resulting solution is shaken for approximately 72 hours in an autoclave at room temperature. The solution is then neutralized with sodium bicarbonate, dried with magnesium sulfate, and then evaporated to yield (+)-t-butyl 2-bromo-3-methylbutyrate.

Workup

  1. dry with materialdried with magnesium sulfate
  2. customevaporated

Sources & evidence

ORD record
ord-3311d92735c44324a2f29d5f4cb91bb7
Source dataset
uspto-grants-1980_08
Patent number
US04219497

Reaction notes

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