Malonic Acid → HCID 86709930, compound

HRID 1019493Notes

Reaction equation

HRID 1019493 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=1)[CH:5]=O.[C:14]([OH:20])(=[O:19])[CH2:15]C(O)=O.C([O-])(=O)C.[NH4+:25]>C(O)(C)C>[NH2:25][CH:5]([C:4]1[CH:7]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=[C:2]([Br:1])[CH:3]=1)[CH2:15][C:14]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 517165Ammonium AcetateHCID 59539639HCID 59539639, compound

Product 1

HCID 86709930HCID 86709930, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 3-bromo-5-tert-butylbenzaldehyde (4.17 g, 17.30 mmol), malonic acid (2.15 g, 20.72 mmol) and ammonium acetate (2.66 g, 34.59 mmol) in isopropanol (35 mL) was heated at reflux under nitrogen for 3 h to afford a thick colorless solid. The solid was filtered hot, washed with hot isopropanol (2×25 mL) and dried in vacuo to give the desired racemic product as a colorless solid (2.68 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 3 h
  3. customto afford a thick colorless solid
  4. filtrationThe solid was filtered hot
  5. washwashed with hot isopropanol (2×25 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2a27ebe6b5bf44d48b7a1e3ba09032fc
Source dataset
uspto-grants-2014_05
Patent number
US08716226B2

Reaction notes

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