Potassium Carbonate → Tert-butyl 2-(4-formyl-3-methoxyphenoxy)acetate

HRID 1078795Notes

Reaction equation

HRID 1078795 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:3][C:4]=1[O:10][CH3:11])=[O:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 5195414-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 19428464Tert-butyl 2-(4-formyl-3-methoxyphenoxy)acetateYield 218%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxy-2-methoxybenzaldehyde (5.23 g; 34.4 mmol), t-butyl bromoacetate (4.9 mL; 30.3 mmol) and K2CO3 (15.1 g; 108.9 mmol) in 50 mL of DMF was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate, filtered, and partitioned between ethyl acetate and 1 N HCl. The organic phase was washed (sat. NaCl) and dried (MgSO4), and concentrated to give 17.59 g of t-butyl 4-formyl-3-methoxyphenoxyacetate as a white solid.

Workup

  1. filtrationfiltered
  2. custompartitioned between ethyl acetate and 1 N HCl
  3. washThe organic phase was washed (sat. NaCl)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f83240ac8894fe4a9862305ece2a2c6
Source dataset
uspto-grants-1996_08
Patent number
US05550215

Reaction notes

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