Methylparaben → Methyl 4-(2-(4-formylphenoxy)ethoxy)benzoate

HRID 416291Notes

Reaction equation

HRID 416291 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[OH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:9]([C:8]1[CH:11]=[CH:12][C:5]([O:4][CH2:3][CH2:2][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=2)=[CH:6][CH:7]=1)=[O:10]

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 2627064-(2-Bromoethoxy)Benzaldehyde

Product 1

HCID 18526174Methyl 4-(2-(4-formylphenoxy)ethoxy)benzoateYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 354 (1.21 g, 5.27 mmol) in DMF (10 mL) was added methyl 4-hydroxybenzoate (0.80 g, 5.27 mmol) and K2CO3 (2.91 g, 21.1 mmol). The resultant mixture was stirred at 60° C. for 6 h, filtered, and evaporated. The residue was purified by silica gel column chromatography, eluent EtOAc-hexane (1:2) to afford title compound (0.83 g, 53%). LRMS (ESI): (calc.) 300.3; (found) 301.4 (MH)+.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was purified by silica gel column chromatography, eluent EtOAc-hexane (1:2)

Sources & evidence

ORD record
ord-7bb264eaa6de47b49e465483cc49eaec
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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