3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

HRID 892857Notes

Reaction equation

HRID 892857 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][C:11](C)([O-])[CH3:12].[K+].BrC(C)C>CS(C)=O.[Cl-].[Na+].O>[CH:11]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([CH3:12])[CH3:10]

Participants

6

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 63582-BromopropaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 7129143-IsopropoxybenzaldehydeYield 57.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-hydroxybenzaldehyde (6.00 g, 49.1 mmol) in DMSO (100 mL) was added potassium t-butoxide (6.34 g, 56.5 mmol) and the resulting mixture was stirred for 20 mins. A sample of 2-bromopropane (7.25 g, 59 mmol) was added and the reaction was stirred for 18 hrs. It was then diluted with brine (100 mL) and extracted with ethylacetate (3×125 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 10:90) to afford 4.61 g (57%) of 3-isopropoxybenzaldehyde as a colorless oil.

Workup

  1. stirringthe reaction was stirred for 18 hrs
  2. extractionextracted with ethylacetate (3×125 mL)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. customThe resulting residue was chromatographed (silica gel, ether:hexanes, 10:90)

Sources & evidence

ORD record
ord-f6c763afa5d342f78ce6ac234746fd59
Source dataset
uspto-grants-1992_06
Patent number
US05120752

Reaction notes

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