Ethylene Glycol → HCID 13814323, compound

HRID 1789369Notes

Reaction equation

HRID 1789369 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8].[CH2:13](O)[CH2:14][OH:15].P(=O)(O)(O)O.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:14]1[O:15][CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH2:3][CH2:2][Cl:1])[O:8][CH2:13]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1004Phosphoric AcidHCID 516892Sodium BicarbonateHCID 38414102-(2-Chloroethoxy)benzaldehyde

Product 1

HCID 13814323HCID 13814323, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 46.5 g of 2-(2-chloroethyloxy)benzaldehyde and 33.2 g of ethylene glycol in 500 ml of benzene in added 0.5 ml of 85% phosphoric acid, and the mixture is refluxed with stirring for about 18 hours while removing the produced water. After the reaction, the reaction mixture is cooled with ice and is made alkaline with saturated sodium bicarbonate solution to separate into two layers. The benzene layer is taken, washed with saturated saline solution, dried and then distilled to remove the solvent. The crude product thus obtained is distilled to give 56 g of 2-(2-chloroethyloxy)benzaldehyde ethyleneacetal (yield: 97%) as a colorless oil. b.p. 130°-135° C./0.3 mmHg.

Workup

  1. customwhile removing the produced water
  2. customAfter the reaction
  3. temperaturethe reaction mixture is cooled with ice
  4. customto separate into two layers
  5. washwashed with saturated saline solution
  6. customdried
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe crude product thus obtained
  10. distillationis distilled

Sources & evidence

ORD record
ord-f5b0b9287b1249399995fc70dd4ff6e7
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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