Dichloromethane → Methyl 2-formylbenzoate

HRID 231402

Reaction equation

HRID 231402 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([OH:3])=[O:2].[CH3:12]OS(OC)(=O)=O.ClCCl.C(N(CC)CC)C>O>[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O:3][CH3:12])=[O:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 8406Phthalaldehydic acidHCID 8471Triethylamine

Product 1

HCID 243003Methyl 2-formylbenzoateYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 3-neck 1-liter round-bottom flask equipped with a magnetic stirrer, reflux condenser and addition funnel was added 2-carboxybenzaldehyde (100.00 g, 0.659 moles), dimethylsulfate (162.8 g 1.291 moles) and 200 ml of dichloromethane under nitrogen. The mixture was heated to reflux and triethylamine (135.89 g, 1.343 moles) was added at such a rate to maintain a brisk reflux. After the addition was complete, the solution was allowed to cool to room temperature and stirred overnight. Water (400 ml) was then added and the layers separated. The aqueous layer was extracted with dichloromethane (1×200 ml) and the combined organic layers washed with saturated sodium bicarbonate solution (1×400 ml), dried over magnesium sulfate and concentrated in vacuo to give a golden oil. Vacuum distillation of this oil gave 88.7 g of the product as a pale yellow oil, bp 95°-98° C./0.4 mm.

Workup

  1. customTo a 3-neck 1-liter round-bottom flask equipped with a magnetic stirrer
  2. temperaturereflux
  3. additioncondenser and addition funnel
  4. temperatureThe mixture was heated
  5. temperatureto reflux
  6. temperatureto maintain a brisk reflux
  7. additionAfter the addition
  8. customthe layers separated
  9. extractionThe aqueous layer was extracted with dichloromethane (1×200 ml)
  10. washthe combined organic layers washed with saturated sodium bicarbonate solution (1×400 ml)
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated in vacuo
  13. customto give a golden oil
  14. distillationVacuum distillation of this oil

Sources & evidence

ORD record
ord-c527a084804249b09e36cc40d8efb2a2
Source dataset
uspto-grants-1989_07
Patent number
US04846873

Linked notes

Loading…