Sulfuric Acid → methyl 4-formylmethyloxybenzoate

HRID 359069Notes

Reaction equation

HRID 359069 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)C.S(=O)(=O)(O)O>O1CCOCC1>[CH:4]([CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)=[O:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 10084384Methyl 4-(2,2-diethoxyethoxy)benzoate

Product 1

HCID 11636984methyl 4-formylmethyloxybenzoateYield 92.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 4-(2,2-diethoxyethoxy)benzoate (36.29 g) was dissolved in dioxane (100 ml), added thereto 2N sulfuric acid (200 ml), and the mixture was heated with stirring at 70° C. for 6 hours. After concentrated under reduced pressure to about half volume, it was diluted with water in two fold, and concentrated again under reduced pressure. The precipitate was collected by filtration, and washed successively with aqueous sodium hydrogencarbonate solution and water to give methyl 4-formylmethoxybenzoate (24.39 g). mp. 58°-60° C.

Workup

  1. additionadded
  2. concentrationAfter concentrated under reduced pressure to about half volume, it
  3. additionwas diluted with water in two fold
  4. concentrationconcentrated again under reduced pressure
  5. filtrationThe precipitate was collected by filtration
  6. washwashed successively with aqueous sodium hydrogencarbonate solution and water

Sources & evidence

ORD record
ord-0927a61171e64dccacce81c9d49f6f22
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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