Malonic Acid → HCID 86737519, compound

HRID 894145Notes

Reaction equation

HRID 894145 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].[Cl:8][CH2:9][C:10](=O)/[CH:11]=[CH:12]/[Cl:13].N1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C1COCC1.O.[Ti](Cl)(Cl)(Cl)Cl>[C:3]([C:2](=[C:11]([CH2:12][Cl:13])/[CH:10]=[CH:9]\[Cl:8])[C:1]([OH:7])=[O:6])([OH:5])=[O:4]

Participants

8

Reactant 3

HCID 867Malonic AcidHCID 1049PyridineHCID 114124261,4-DICHLORO-3-BUTEN-2-ONE

Product 1

HCID 86737519HCID 86737519, compoundYield 15.6%

Reagents, catalysts & solvents 4

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Titanium tetrachloride (2.5 ml., 25 mmol) in carbon tetrachloride (7.5 ml) was added to THF (60 ml) at 0° C. Malonic acid (1.0 g., 10 mmol) and trans 1,4-dichlorobut-3-en-2-one (1.4 g., 10 mmol) in THF (10 ml) was added. Pyridine (3.3 ml., 40 mmol) in THF (10 ml) was added dropwise over fifteen minutes at 0° C. The reaction mixture was stirred at room temperature for three hours, diluted with water (50 ml) and extracted with ether (50 ml., 2×25 ml). The extracts were washed with brine, N sodium bicarbonate solution, brine, dried (Na2SO4) and evaporated to give the title product (0.35 g., 12%). δ (CDCl3) 5.00 (2H, s, CH2), 6.91 (1H, d, J 5 Hz, CH=), 8.01 (1H, d, J 5 Hz, CH=), 9.68 (2H, s, --OH). νmax (CHCl3) 1720 cm-1.

Workup

  1. extractionextracted with ether (50 ml., 2×25 ml)
  2. washThe extracts were washed with brine, N sodium bicarbonate solution, brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-197f221ec5cb404195e116d387616302
Source dataset
uspto-grants-1981_08
Patent number
US04282373

Reaction notes

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