Hydrochloric Acid → 5-Methoxy-2-methylbenzaldehyde

HRID 322980Notes

Reaction equation

HRID 322980 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:14])=[C:7]([CH:9]2OCC[O:10]2)[CH:8]=1.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:14])=[C:7]([CH:8]=1)[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 221712332-(5-Methoxy-2-methylphenyl)-[1,3]dioxolane

Product 1

HCID 123475665-Methoxy-2-methylbenzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(5-methoxy-2-methylphenyl)-[1,3]dioxolane (18.25 g) in tetrahydrofuran (180 mL) is treated with 1 N hydrochloric acid (27 mL). The reaction mixture is heated at reflux for 2 hours, evaporated and the residue is partitioned between ethyl acetate (150 mL) and water (150 mL). The organic phase is washed with water (150 mL), with brine (150 mL), dried over magnesium sulphate and evaporated to give 5-methoxy-2-methylbenzaldehyde (12 g) as an orange oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. customevaporated
  4. customthe residue is partitioned between ethyl acetate (150 mL) and water (150 mL)
  5. washThe organic phase is washed with water (150 mL), with brine (150 mL)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-a774fa27220d406eacbe8f1c3ab5aab3
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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