Malonic Acid → HCID 11543803, compound

HRID 1065530Notes

Reaction equation

HRID 1065530 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].C(Cl)(=O)C.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1>>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[C:2]([C:1]([OH:7])=[O:6])[C:3]([OH:5])=[O:4])=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 867Malonic AcidHCID 6367Acetyl chlorideHCID 77264-Chlorobenzaldehyde

Product 1

HCID 11543803HCID 11543803, compoundYield 61%

Conditions

Temperature
65 °C

Procedure

Under nitrogen, malonic acid (powdered, 20 g., 0.192 mole) was mixed with acetyl chloride (15 g., 0.192 mole) and heated to 65° C. in an oil bath. p-Chlorobenzaldehyde (21.6 g., 0.153 mole) was added and the mixture further heated to 80° C. A yellow, slowly refluxing solution resulted, followed by copious precipitation of solids. The mixture was cooled and product recovered by filtration, resuspended in water, stirred for 5 minutes and refiltered to yield title product [21.1 g.; 61% of theory; m.p. 215° C. (dec.)].

Workup

  1. temperaturethe mixture further heated to 80° C
  2. customA yellow, slowly refluxing solution resulted
  3. customfollowed by copious precipitation of solids
  4. temperatureThe mixture was cooled
  5. filtrationproduct recovered by filtration

Sources & evidence

ORD record
ord-f52b16a89d9b48e894512487c966e342
Source dataset
uspto-grants-1982_05
Patent number
US04329495

Reaction notes

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