Water → HCID 239549, compound

HRID 1935982Notes

Reaction equation

HRID 1935982 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Cl:10][CH2:11][CH:12]([OH:15])[CH2:13]O.O>CC1C=CC(S(O)(=O)=O)=CC=1.CCCCCC>[CH3:5][C:3]1([CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])[O:15][CH:12]([CH2:11][Cl:10])[CH2:13][O:4]1

Participants

6

Reactant 3

HCID 962WaterHCID 72903-Chloro-1,2-propanediolHCID 8868Ethyl Acetoacetate

Product 1

HCID 239549HCID 239549, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8058HexaneSolvent

Procedure

In a similar manner to the preceding Examples, 65 g (0.5 mol) of ethyl acetoacetate are heated together with 55 g (0.5 mol) of 3-chloro-1,2-propanediol and 0.2 g of p-TSA in a water separator. 100 ml of hexane act as entraining agent. Once 9 ml of water have separated, the reaction mixture is washed with 100 ml of water, to which 1 g of NaOH is added, dried over Na2SO4 and fractionated. 80 g (72%) of 2-methyl-2-ethoxycarbonylmethyl-4-chloromethyl-1,3-dioxolane are obtained. Bp.: 124° C. (1500 Pa); IR: 1736 cm−1 (C═O, ester); MS: m/e=207 (M−15), 181, 173, 157, 144, 135, 115, 99, 75, 57, 43.

Workup

  1. customOnce 9 ml of water have separated
  2. washthe reaction mixture is washed with 100 ml of water, to which 1 g of NaOH
  3. additionis added
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-da2b8564fa5c40499e6b0ab580a75d18
Source dataset
uspto-grants-2002_05
Patent number
US06388104B1

Reaction notes

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