3,5-Dimethyl-4-hydroxybenzaldehyde → HCID 23046188, compound

HRID 2107644Notes

Reaction equation

HRID 2107644 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:11].C(N(CC)C(C)C)(C)C.[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26]Cl>ClCCCl>[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26][O:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([CH:6]=[O:7])=[CH:8][C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531Diisopropylethylamine

Product 1

HCID 23046188HCID 23046188, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-hydroxy-3,5-dimethylbenzaldehyde (5 g), N,N-diisopropylethylamine (6.9 ml), (2-methoxyethoxy)methylchloride (4.26 ml) and 1,2-dichloroethane (65 ml) was refluxed for 5 hours. The reaction mixture was washed with water and dried over magnesium sulfate. After removal of the solvent, the residue was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate (8:2 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure to give 4-[(2-methoxyethoxy)methoxy]-3,5-dimethylbenzaldehyde (6.54 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customAfter removal of the solvent
  5. washeluted with a mixture of n-hexane and ethyl acetate (8:2 V/V)
  6. additionThe fractions containing the object compound
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f4a0cd654eb4630b3966c8fe47768ba
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

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