Potassium Carbonate → 5-(3,3-Dimethylbutoxy)-2-hydroxybenzaldehyde

HRID 1023875Notes

Reaction equation

HRID 1023875 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].I[CH2:18][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[CH3:21][C:20]([CH3:23])([CH3:22])[CH2:19][CH2:18][O:10][C:7]1[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 709492,5-DihydroxybenzaldehydeHCID 148248991-Iodo-3,3-dimethylbutane

Product 1

HCID 866730205-(3,3-Dimethylbutoxy)-2-hydroxybenzaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 2,5-dihydroxybenzaldehyde in DMF was added K2CO3 at room temperature and the mixture was stirred for 10 min. To this solution 1-iodo-3,3-dimethylbutane was added. After stirring at 70° C. for 4 h, the solvent was removed under reduced pressure and reaction mixture was diluted with ethyl acetate. After washing with water, the organic layer was dried over Na2SO4 and concentrated under vacuum. The crude product was purified by column chromatography to give desired product in 65% yield. 1H NMR: 0.97 (s, 9H), 1.73 (t, 2H, J=7.2 Hz), 4.05 (t, 2H, J=7.2 Hz), 6.88 (d, 1H, J=9.2 Hz), 7.09 (dd, 1H, J=9.2, 3.2 Hz), 7.35 (d, 1H, J=3.2 Hz), 10.39 (s, 1H)

Workup

  1. stirringAfter stirring at 70° C. for 4 h
  2. customthe solvent was removed under reduced pressure and reaction mixture
  3. additionwas diluted with ethyl acetate
  4. washAfter washing with water
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-a165e8daf5cc4a7c93f16163e4ae3430
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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