Ethanol → 2-Chloro-1,1-diethoxy-2-methylpropane

HRID 1769050Notes

Reaction equation

HRID 1769050 reaction equation
[Cl:1][C:2](C)([CH3:5])[CH:3]=O.C(O)C.C(O[CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])C>C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>[CH2:18]([O:17][CH:13]([O:14][CH2:15][CH3:16])[C:2]([Cl:1])([CH3:5])[CH3:3])[CH3:19]

Participants

7

Reactant 3

HCID 702EthanolHCID 13513Propanal, 2-chloro-2-methyl-HCID 31214Ethyl orthoformate

Product 1

HCID 151862272-Chloro-1,1-diethoxy-2-methylpropaneYield 68.2%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 11430Potassium CarbonateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 45 g (0.424 mol) of 2-chloro-2-methylpropanal, 99.6 ml (1.69 mol) of ethanol, 81.6 g (0.55 mol) of triethylorthoformate in 100 ml of methylene chloride was added 800 mg (4.2 mmol) of p-toluenesulfonic acid and the mixture was stirred at room temperature. After adding 2 g of potassium carbonate to the above mixture, the reaction mixture was stirred (2 min.), and filtered. The filtrate was concentrated (80° C.) to remove methylene chloride and the residue was distilled (2×) to afford 52 g (68.2%) of 2-chloro-2-methylpropanal diethyl acetal, b.p. 55°-65° C./25 mm.

Workup

  1. stirringthe reaction mixture was stirred (2 min.)
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated (80° C.)
  4. customto remove methylene chloride
  5. distillationthe residue was distilled (2×)

Sources & evidence

ORD record
ord-894c34e1de6e40329269814b41dca283
Source dataset
uspto-grants-1995_01
Patent number
US05380729

Reaction notes

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