Pivalaldehyde → HCID 68047232, compound

HRID 658559Notes

Reaction equation

HRID 658559 reaction equation
[CH3:1][C:2]([CH:5]=O)([CH3:4])[CH3:3].[CH3:7][O:8][C:9]1[C:10]([CH3:19])=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([NH:14][NH2:15])=[O:13]>CO.C(O)(=O)C>[CH3:4][C:2]([CH3:1])([CH3:3])[CH:5]=[N:15][NH:14][C:12](=[O:13])[C:11]1[CH:16]=[CH:17][CH:18]=[C:9]([O:8][CH3:7])[C:10]=1[CH3:19]

Participants

5

Reactant 2

HCID 12417PivalaldehydeHCID 450912733-Methoxy-2-methylbenzohydrazide

Product 1

HCID 68047232HCID 68047232, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

Pivaldehyde (13.45 g, 156 mmoles) was dissolved in 300 mL methanol in a round bottom flask. 3-methoxy-2-methyl-benzoic acid hydrazide (26.6 g, 147.6 mmoles) and 150 drops glacial acetic acid were added, and the mixture was heated at reflux for ca. 8 hours, while monitoring by TLC. Upon completion of the reaction, the solvent was removed in vacuo, and the product was slurried in cold hexanes and filtered on a Büchner funnel to provide 24.4 g (66%) of 3-methoxy-2-methyl-benzoic acid (2,2-dimethyl-propylidene)-hydrazide. Rf=0.19, (2:1 hexanes:ethyl acetate); 1H NMR (400 MHz, DMSO-d6) δ 7.42+7.41 (3 s, 1H), 7.1 (t, 1H), 6.9 (d, 1H), 6.82 (d, 1H), 3.78 (s, 3H), 2.2+2.1 (2 s, 3H), 1.07+1.0 (3 s, 9H), multiple conformations, possibly E/Z mixture.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for ca. 8 hours, while monitoring by TLC
  3. customUpon completion of the reaction
  4. customthe solvent was removed in vacuo
  5. filtrationfiltered on a Büchner funnel

Sources & evidence

ORD record
ord-d07e1497b08e4c1f9e2e6b941c4d7b6d
Source dataset
uspto-grants-2011_12
Patent number
US08076517B2

Reaction notes

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