Malonic Acid → HCID 86709930, compound

HRID 1526764Notes

Reaction equation

HRID 1526764 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 74.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 3-bromo-5-tert-butylbenzaldehyde (41.5 g, 0.17 mol), malonic acid (21.5 g, 0.20 mol) and ammonium acetate (26.6 g, 0.34 mol) in isopropanol (350 mL) was heated at reflux under nitrogen for 14 h to afford a thick colorless solid. The solid was filtered hot, washed with hot isopropanol (2×100 mL) and dried in vacuo to give the desired racemic product as a colorless solid (37.8 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 14 h
  3. customto afford a thick colorless solid
  4. filtrationThe solid was filtered hot
  5. washwashed with hot isopropanol (2×100 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-7b96fb5a185049e1a4b4136a127cfa63
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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