3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

HRID 594269Notes

Reaction equation

HRID 594269 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].I[CH:11]([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOCC>[CH:11]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 11430Potassium Carbonate

Product 1

HCID 7129143-Isopropoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of commercially available 3-hydroxybenzaldehyde (3.000 g; 24.60 mmol), 2-iodopropane (12.528 g; 73.70 mmol), K2CO3 (6.790 g; 49.10 mmol), and Cs2CO3 (1.601 g; 4.91 mmol) in anh. DMF (60 ml) was stirred at rt, under nitrogen, for 17 h. Et2O was added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 3-isopropoxybenzaldehyde as a yellow oil. LC-MS (conditions A): tR=0.76 min.; [M+H]+: 165.24 g/mol.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2fc9255129084ec1a5ce6a309044e9cd
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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