Water → 2,3-Diisopropoxy-4-methoxybenzaldehyde

HRID 9308

Reaction equation

HRID 9308 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:13]([O-])([O-])=O.[K+].[K+].Br[CH:20]([CH3:22])[CH3:21].O.CCO[C:27]([CH3:29])=O>CN(C=O)C>[CH:20]([O:1][C:2]1[C:9]([O:10][CH:27]([CH3:29])[CH3:13])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])([CH3:22])[CH3:21]

Participants

7

Reactant 5

HCID 962WaterHCID 63582-BromopropaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 115573522,3-Dihydroxy-4-methoxybenzaldehyde

Product 1

HCID 219865542,3-Diisopropoxy-4-methoxybenzaldehydeYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 21 (26.70 g, 158.7 mmol) in DMF (150 mL) under nitrogen, was added K2CO3 (65.84 g, 476.3 mmol) followed by 2-bromopropane (44.72 mL, 476.3 mmol) and heated to reflux (90° C.) for 12 hours. Water (200 mL) and EtOAc (200 mL) were added to the reaction mixture, the phases were separated, and the aqueous phase was extracted with EtOAc (3×200 mL). The combined organic solutions were dried over MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, elution with hexane) provided 32.85 g (1.30.2 mmol, 82%) of the diusopropyl-protected aldehyde 22 as a yellow oil.

Workup

  1. temperatureheated
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (3×200 mL)
  4. dry with materialThe combined organic solutions were dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification
  7. washby flash column chromatography (silica gel, elution with hexane)

Sources & evidence

ORD record
ord-fcacfd8cbe564e93b9260f019b289944
Source dataset
uspto-grants-2006_08
Patent number
US07091240B2

Linked notes

Loading…