3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

HRID 1488474Notes

Reaction equation

HRID 1488474 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].I[CH:17]([CH3:19])[CH3:18].O>CN(C=O)C>[CH:17]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 7129143-Isopropoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

50 g of 3-hydroxybenzaldehyde are dissolved, under nitrogen, in 250 ml of DMF. 60 g of K2CO3 and then 60 ml of 2-iodopropane are added and the reaction mixture is heated for 18 hours at 50° C. and poured into 2.5 liters of water. Extraction is carried out with ethyl ether and the ether phase is washed with a dilute solution of NaOH, dried over MgSO4 and concentrated under vacuum to give 53.5 g of an oil.

Workup

  1. extractionExtraction
  2. washthe ether phase is washed with a dilute solution of NaOH
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5ddfe74d0102419f9771800e01e16e86
Source dataset
uspto-grants-1997_10
Patent number
US05674881

Reaction notes

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