4-Hydroxybenzaldehyde → 4-Propoxybenzaldehyde

HRID 710415Notes

Reaction equation

HRID 710415 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:11]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 78401-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 798124-PropoxybenzaldehydeYield 82.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (0.5 g, 4.1 mmol), 1-bromopropane (0.3 ml) and K2CO3 (0.69 g, 5 mmol) in anhydrous DMF (5 ml) was stirred for 1 h at reflux. This was diluted to 100 ml with EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title compound (0.55 g, 82.3%), as yellow oil 1H-NMR (CDCl3) 1.0 (tr, 3H, J=7.41 Hz); 1.7-2.0 (m, 2H); 3.95 (tr, 2H, J=6.57 Hz); 6.95 (d, 2H, J=8.73 Hz); 8.00 (d, 2H, J=8.76 Hz).

Workup

  1. temperatureat reflux
  2. washwashed with H2O
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-5e6e5ac2247a4342ae6ec242a9a45c08
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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