Acetic Acid → HCID 20461265, compound

HRID 851445Notes

Reaction equation

HRID 851445 reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][CH:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[C:4](=[O:15])[O:3]1.C=O.[OH-].C[N+](C)(C)C.[C:25](O)(=[O:27])C>N1C=CC=CC=1.CO>[CH3:1][C:2]1([CH3:16])[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])([CH2:25][OH:27])[C:4](=[O:15])[O:3]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 60966Tetramethylammonium hydroxideHCID 20461267HCID 20461267, compound

Product 1

HCID 20461265HCID 20461265, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent2×

Conditions

Temperature
-5 °C

Procedure

104.4 g (0.4 mole) of 2,2-dimethyl-4-(2,4-dichlorophenyl)-1,3-dioxolan-5-one are dissolved in 700 ml of pyridine and to the solution are added 48 g of paraformaldehyde. Then 40 ml of a 40% solution of tetramethylammonium hydroxide in methanol are slowly added dropwise. The mixture is stirred for 12 hours, cooled to -5° C., and a solution of 100 ml of glacial acetic acid and 400 ml of pyridine is added dropwise until the pH value is 6.5 to 7. The reaction solution is poured into ice-water and extracted with methylene chloride. The extract is dried over sodium sulfate and the product is crystallised by addition of diethyl ether. The crystalline precipitate is washed with a small amount of diethyl ether and petroleum ether. It has a melting point of 182°-185° C.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe extract is dried over sodium sulfate
  3. customthe product is crystallised by addition of diethyl ether
  4. washThe crystalline precipitate is washed with a small amount of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-6be43e05757d4210afa18f4cacc7e107
Source dataset
uspto-grants-1983_05
Patent number
US04384879

Reaction notes

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