Sodium Chloride → HCID 20484759, compound

HRID 648128Notes

Reaction equation

HRID 648128 reaction equation
[CH2:1]([C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Na+].[CH3:21][O:22]C(Cl)Cl>ClCCl>[CH2:13]([O:12][C:10]([C:9]1[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=1[CH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:21]=[O:22])=[CH:6][CH:7]=1)=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 21004Methane, dichloromethoxy-HCID 13236168HCID 13236168, compound

Product 1

HCID 20484759HCID 20484759, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-benzylbenzoate (54.0 g) was dissolved in 100 ml of dichloromethane, and with stirring, 121.3 g of stannic chloride was added while cooling the solution with a mixture of ice and sodium chloride. The mixture was stirred for 1 hour. Subsequently, 86 g of α,α-dichloromethyl methyl ether was added dropwise over 1 hour, and then the mixture was stirred at room temperature for 3 hours. After the reaction, the reaction mixture was poured into 1 liter of ice water, and stirred. The dichloromethane layer was separated, washed with water, a saturated aqueous solution of sodium carbonate and subsequently with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The dichloromethane was distilled off. To the residue was added 250 ml of a saturated aqueous solution of sodium bisulfite, and the mixture was vigorously stirred. The precipitated crystals were collected by filtration, and washed with 100 ml of a saturated aqueous solution of sodium chloride and then with 100 ml of ether. The crystals were then suspended in 500 ml of water, and with stirring, 120 g of sodium carbonate was added little by little over the course of 15 minutes. The mixture was stirred for 2 hours. The separated oily substance was extracted with 300 ml of ether. The ethereal layer was washed with water and dried over anhydrous magnesium sulfate. The ether was distilled off to afford 43.3 g of 4-(2-ethoxycarbonylbenzyl)benzaldehyde as a red oily substance.

Workup

  1. temperaturewhile cooling the solution
  2. stirringThe mixture was stirred for 1 hour
  3. stirringthe mixture was stirred at room temperature for 3 hours
  4. customAfter the reaction
  5. stirringstirred
  6. customThe dichloromethane layer was separated
  7. washwashed with water
  8. dry with materiala saturated aqueous solution of sodium carbonate and subsequently with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  9. distillationThe dichloromethane was distilled off
  10. additionTo the residue was added 250 ml of a saturated aqueous solution of sodium bisulfite
  11. stirringthe mixture was vigorously stirred
  12. filtrationThe precipitated crystals were collected by filtration
  13. washwashed with 100 ml of a saturated aqueous solution of sodium chloride
  14. stirringwith stirring
  15. addition120 g of sodium carbonate was added little by little over the course of 15 minutes
  16. stirringThe mixture was stirred for 2 hours
  17. extractionThe separated oily substance was extracted with 300 ml of ether
  18. washThe ethereal layer was washed with water
  19. dry with materialdried over anhydrous magnesium sulfate
  20. distillationThe ether was distilled off

Sources & evidence

ORD record
ord-4c3ca8fc617e4d5eb6dec4d7ce92905a
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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