3-Hydroxybenzaldehyde → 3-(2-Methoxyethoxy)benzaldehyde

HRID 2416998Notes

Reaction equation

HRID 2416998 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Br[CH2:11][CH2:12][O:13][CH3:14].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH3:14][O:13][CH2:12][CH2:11][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 64855613-(2-Methoxyethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.0 g of 3-hydroxybenzaldehyde, 1.1 g of 1-bromo-2-methoxyethane, and 10.7 g of Cs2CO3 were stirred at 40° C. in 10 ml of DMF (anhydrous) for 4 hours. The mixture was diluted with 100 ml of water and extracted twice with, in each case, 50 ml of EA. The extract was dried over MgSO4 and the solvent was removed under reduced pressure. This gave 1.3 g of a colorless oil.

Workup

  1. extractionextracted twice with, in each case, 50 ml of EA
  2. dry with materialThe extract was dried over MgSO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5c9b50a7b74b465d8ea3ba3b01009432
Source dataset
uspto-grants-2004_11
Patent number
US06825231B2

Reaction notes

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