Dimethyl Sulfate → 4-Benzyloxy-2-methoxy-3-methyl-benzaldehyde

HRID 929100Notes

Reaction equation

HRID 929100 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:17])[C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19]OS(OC)(=O)=O.[OH-].[Na+].O1CCOCC1>O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([O:17][CH3:19])[C:10]=1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 597616904-(Benzyloxy)-2-hydroxy-3-methylbenzaldehyde

Product 1

HCID 597617644-Benzyloxy-2-methoxy-3-methyl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 4-benzyloxy-2-hydroxy-3-methyl-benzaldehyde (1.57 g, 6.49 mmol), dimethylsulfate (1.04 ml, 10.9 mmol), NaOH (1.02 g, 25.5 mmol), 1,4-dioxane (20 mL) and water (10 mL) was stirred at 90° C. for 6 h. The reaction mixture was cooled to RT, water (100 mL) was added, extracted with EtOAc (150 mL). The extract was washed with brine (100 mL), dried over Na2SO4 and evaporated. The residue was purified on SiO2 (25 g) column, hexane to toluene. Yield 1.20 g (4.68 mmol, 72%), white solid. 1H NMR (300 MHz, DMSO): δ 10.11 (s, 1H), 7.64 (d, J=8.9 Hz, 1H), 7.49-7.32 (m, 5H), 7.05 (d, J=8.9 Hz, 1H), 5.24 (s, 2H), 3.81 (s, 3H), 2.14 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with EtOAc (150 mL)
  3. washThe extract was washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified on SiO2 (25 g) column, hexane to toluene

Sources & evidence

ORD record
ord-17635ebc867d4da2906c01b4a6573843
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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