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

HRID 2061034Notes

Reaction equation

HRID 2061034 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][C:6]([CH3:11])=[CH:7][C:8]([OH:10])=[O:9]>O.C(O)(=O)C>[N:1]([C:6]([CH3:11])([CH3:5])[CH2:7][C:8]([OH:10])=[O:9])=[N+:2]=[N-:3]

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

According to the method of S, Nagarajan and B. Ganem, J. Org. Chem., 51, 4856, (1986), sodium azide (52 g, 0.8 mol) in water (100 mL) was added to a stirred solution of 3,3-dimethylacrylic acid (20 g, 0.2 mol) in glacial acetic acid (50 mL) in one portion. The clear yellow solution was stirred for 1 h at RT, 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.

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-ccd8410d9e1241a2a552f451e8da78fa
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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