Hydrochloric Acid → Ethyl 2-chloro-2-ethoxyacetate

HRID 126953

Reaction equation

HRID 126953 reaction equation
CO[CH2:3][CH2:4]OC.C(O)C.[ClH:10].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[O:13]>O>[Cl:10][CH:12]([O:13][CH2:3][CH3:4])[C:11]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 80711,2-DimethoxyethaneHCID 70211Ethyl oxoacetate

Product 1

HCID 2724873Ethyl 2-chloro-2-ethoxyacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a mixture of 10 ml. of 1,2-dimethoxyethane and 5.8 ml. of ethanol is passed 3.65 g. hydrogen chloride gas with cooling. Then 10.2 g of ethyl glyoxylate is added and after 24 hours at 25° C., 200 ml. of water and ice is added. The mixture is then extracted several times with ether and the extracts dried over anhydrous sodium sulfate. After evaporation of the extracts to an oil, the ethyl α-chloro-α-ethoxy-acetate so formed is added to a stirred mixture of 35.0 g. of sodium 4-(hexadecylamino)benzoate in 125 ml. of hexamethylphosphoramide. After 24 hours at 20° C., the product is obtained as white crystals by careful addition of water.

Workup

  1. additionInto a mixture of 10 ml
  2. extractionThe mixture is then extracted several times with ether
  3. dry with materialthe extracts dried over anhydrous sodium sulfate
  4. customAfter evaporation of the extracts to an oil

Sources & evidence

ORD record
ord-366d262e502f480a8aabd130c51c6a61
Source dataset
uspto-grants-1981_03
Patent number
US04254138

Linked notes

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