Hydrochloric Acid → 1,3-Diethyl 2-[(2-iodophenyl)methyl]propanedioate

HRID 1432042Notes

Reaction equation

HRID 1432042 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3].Cl[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[I:21].[Cl-].[Na+].Cl>C(O)C>[CH2:2]([O:4][C:5](=[O:12])[CH:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[I:21])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7761Diethyl Malonate2×HCID 1010641-(Chloromethyl)-2-iodobenzeneHCID 5360545Sodium

Product 1

HCID 141722941,3-Diethyl 2-[(2-iodophenyl)methyl]propanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (0.19 g, 8.2 mmol) was dissolved in absolute ethanol (12 mL). The solution was cooled on an ice bath. Malonic acid diethyl ester (1.3 g, 8.1 mmol) was added. A solution of 1-chloromethyl-2-iodo-benzene (2.0 g, 7.9 mmol) in absolute ethanol (6 mL) cooled on an ice bath was added to the malonic acid diethyl ester solution. The solution, which deposited sodium chloride, was let stand at 0° C. for 4 h and at room temperature overnight. The solution was neutralised with HCl (4N). The solvent was removed in vacuo and the residue was dissolved in dichloromethane (25 mL). Water (15 mL) was added and the phases were separated. The aqueous phase was reextracted with dichloromethane (10 mL). The combined organic fractions were dried (Na2SO4), filtered and evaporated. Yield: 2.86 g, 92%.

Workup

  1. temperatureThe solution was cooled on an ice bath
  2. customat 0° C.
  3. customfor 4 h
  4. customat room temperature
  5. customovernight
  6. customThe solvent was removed in vacuo
  7. dissolutionthe residue was dissolved in dichloromethane (25 mL)
  8. additionWater (15 mL) was added
  9. customthe phases were separated
  10. dry with materialThe combined organic fractions were dried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-d6507ea1ea79421dae3184b1b00888d0
Source dataset
uspto-grants-2009_11
Patent number
US07612068B2

Reaction notes

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