2,4-Dihydroxybenzaldehyde → 2-hydroxy-4-(3methylbut-2-enyloxy)benzaldehyde

HRID 1603167Notes

Reaction equation

HRID 1603167 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].[CH3:13][C:14]([CH3:18])=[CH:15][CH2:16]Br>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:13][C:14]([CH3:18])=[CH:15][CH2:16][O:12][C:10]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:3])[CH:11]=1

Participants

6

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 14797Potassium HydroxideHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 108674672-hydroxy-4-(3methylbut-2-enyloxy)benzaldehydeYield 17.3%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6 g (0.11 mol) of potassium hydroxide, 22.7 g (0.1 mol) of benzyltriethylammonium chloride, and 14 g (0.1 mol) of 2,4-dihydroxybenzaldehyde was concentrated in vacuo. The residue was suspended in 100 ml of ethyl acetate and 11.7 ml (0.1 mol) of dimethylallyl bromide was slowlv added to the solution. The mixture was extracted with 100 ml of water, and the organic phase was dried and concentrated in vacuo to give 3.568 g of a residue, from which 4.738 g (20%) of 4-(3-methyl)-but-2-enyloxy-2-hydroxybenzaldehyde identical to that previously described by S. Khan, and M. Krishnamurti in Indian J. Chem. 22B (1983), 276 was purified by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 200 g) using petroleum ether-ethyl acetate (9:1) as an eluent.

Workup

  1. extractionThe mixture was extracted with 100 ml of water
  2. customthe organic phase was dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e2fcd4e4b66447baf30e2a412b4e875
Source dataset
uspto-grants-1999_11
Patent number
US05985935

Reaction notes

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