3-Methyl-2-butenoic acid → 3-Azido-3-methylbutanoic acid

HRID 1770701Notes

Reaction equation

HRID 1770701 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([OH:6])=[O:5].[N-:8]=[N+:9]=[N-:10].[Na+]>C(O)(=O)C.O>[N:8]([C:2]([CH3:7])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5])=[N+:9]=[N-:10]

Participants

5

Reactant 2

HCID 109313-Methyl-2-butenoic acidHCID 33557Sodium Azide

Product 1

HCID 596147673-Azido-3-methylbutanoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 3,3-dimethylacrylic acid (20 g, 0.2 mol) in glacial acetic acid (50 mL) was added a solution of sodium azide (52 g, 0.8 mol) in water (100 mL) in one portion. The clear yellow solution was stirred for 1 hour at room temperature and then heated in an oil bath at 95° C. for 2 days. Water (50 mL) was added to the cooled orange solution. This solution was poured into a separatory funnel and extracted with ether (5×200 mL). The combined organic extracts were dried over anhydrous MgSO4 and concentrated to an orange oil. This oil was used without further purification. 1H NMR (CDCl3, 400 MHz): δ 1.44 (s, 6H), 2.55 (s, 2H), 11.80 (bs, 1H).

Workup

  1. temperatureheated in an oil bath at 95° C. for 2 days
  2. additionThis solution was poured into a separatory funnel
  3. extractionextracted with ether (5×200 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  5. concentrationconcentrated to an orange oil
  6. customThis oil was used without further purification

Sources & evidence

ORD record
ord-b9f9b686c9434064adfa7e0485b2cb4a
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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