Methanol → HCID 23510459, compound

HRID 1883197Notes

Reaction equation

HRID 1883197 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH:6]=1)=[O:4].[CH2:13]([OH:17])[CH2:14][CH2:15][OH:16].CO.[OH-].[Na+]>C1(C)C=CC=CC=1.C1COCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:16]1[CH2:15][CH2:14][CH2:13][O:17][CH:11]1[C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 104421,3-PropanediolHCID 14798Sodium HydroxideHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 23510459HCID 23510459, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
111 °C

Procedure

Under nitrogen atmosphere, to a solution of methyl terephthalaldehydate (10.0 g) in toluene (200 mL) were added p-toluenesulfonic acid monohydrate (130 mg) and 1,3-propanediol (5.56 g), and the mixture was stirred at 111° C. for 3.5 hours. The mixture was cooled to room temperature, washed twice with a NaHCO3 solution, and dried over MgSO4. The solvent was evaporated under reduced pressure to give crude methyl 4-(1,3-dioxan-2-yl)benzoate (14.2 g). To a solution of this compound (14.2 g) in THF (150 mL)-MeOH (150 mL) was added a 6N NaOH solution (50.8 mL), and the mixture was stirred at room temperature for 78 hours. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate, and thereto was added a 6N aqueous hydrochloric acid to adjust the pH value thereof to pH=2. The precipitated solid was collected by filtration to give 4-(1,3-dioxan-2-yl)benzoic acid (11.725 g, 93%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed twice with a NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated under reduced pressure
  5. customto give crude methyl 4-(1,3-dioxan-2-yl)benzoate (14.2 g)
  6. stirringthe mixture was stirred at room temperature for 78 hours
  7. customThe solvent was evaporated under reduced pressure
  8. washthe residue was washed with ethyl acetate
  9. additionwas added a 6N aqueous hydrochloric acid
  10. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-1cdf0f1869454563a7b4a0eb26c1c63b
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

Loading…