Malonic Acid → 4-(Allyloxycarbonyl)benzoic acid

HRID 2268213Notes

Reaction equation

HRID 2268213 reaction equation
[CH:1]([C:3]1[CH:14]=[CH:13][C:6]([C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])=[CH:5][CH:4]=1)=[O:2].C(O)(=O)CC(O)=[O:18].CCC1(CC)C(=O)NCCC1=O>N1C=CC=CC=1>[CH2:10]([O:9][C:7]([C:6]1[CH:13]=[CH:14][C:3]([C:1]([OH:18])=[O:2])=[CH:4][CH:5]=1)=[O:8])[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 64653,3-Diethyl-2,4-piperidinedioneHCID 18381245Allyl 4-formylbenzoate

Product 1

HCID 183498554-(Allyloxycarbonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

17.2 g (90.5 mmol) of allyl 4-formylbenzoate, 24 g (230 mmol) of malonic acid, 8 ml of piperidione and 100 ml of pyridine are introduced into a round-bottomed flask. The reaction medium is heated at 100° C. for six hours and then evaporated to dryness. The residue is taken up in water and dichloromethane and acidified to pH 1, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The solid obtained is triturated from hexane, filtered off and dried. 16.7 g (80%) of 4-allyloxycarbonylbenzoic acid, with a melting point of 205-6° C., are collected.

Workup

  1. customevaporated to dryness
  2. customthe organic phase is separated out after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe solid obtained
  6. customis triturated from hexane
  7. filtrationfiltered off
  8. customdried
  9. custom16.7 g (80%) of 4-allyloxycarbonylbenzoic acid, with a melting point of 205-6° C., are collected

Sources & evidence

ORD record
ord-95b2db39e87e42c7b1797e56b2fe9160
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

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