4-Hydroxybenzaldehyde → 4-Methoxymethoxybenzylalcohol

HRID 584383Notes

Reaction equation

HRID 584383 reaction equation
[CH3:1][O:2][CH2:3]Cl.[OH:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C.CCCCCC.O>[CH3:1][O:2][CH2:3][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium Carbonate

Product 1

HCID 116079844-MethoxymethoxybenzylalcoholYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Chloromethyl methyl ether (34.2 ml) was added to a mixture of 4-hydroxybenzaldehyde (50.0 g), potassium carbonate (84.9 g) and N,N-dimethylformaldehyde (150 ml) at 0° C. and stirred at room temperature for 11 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in tetrahydrofuran (300 ml) and methanol (50 ml) and sodium borohydride (7.76 g) was added in portions at 0° C. After stirring for 30 minutes, water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain 4-methoxymethoxybenzylalcohol (56.7 g, yield 82%) as a colorless oil from an ethyl acetate-hexane (2:3, v/v) eluted fraction.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in tetrahydrofuran (300 ml)
  6. additionmethanol (50 ml) and sodium borohydride (7.76 g) was added in portions at 0° C
  7. stirringAfter stirring for 30 minutes
  8. additionwater was added to the reaction mixture
  9. extractionextracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-57e09afed0d543b88ab016e02c7690cc
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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