Ethyl 5-bromovalerate → Pentanoic acid, 5-(4-formyl-3,5-dimethoxyphenoxy)-, ethyl ester

HRID 495847Notes

Reaction equation

HRID 495847 reaction equation
[CH:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([OH:11])=[CH:5][C:4]=1[O:12][CH3:13])=[O:2].CC(C)([O-])C.[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O>[CH:1]([C:3]1[C:4]([O:12][CH3:13])=[CH:5][C:6]([O:11][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:7][C:8]=1[O:9][CH3:10])=[O:2]

Participants

5

Reactant 3

HCID 84580Ethyl 5-bromovalerateHCID 5298942,6-Dimethoxy-4-hydroxybenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 11001390Pentanoic acid, 5-(4-formyl-3,5-dimethoxyphenoxy)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-formyl-3,5-dimethoxyphenol (22.6 g, 124 mmol) and potassium tert-butoxide (15.3 g, 136 mmol) in dimethylformamide (125 mL) was added ethyl 5-bromovalerate (28.5 g, 136 mmol) in dimethylformamide (125 mL) over a period of 20 min. The mixture was heated at 11 0° C. for 6 h and concentrated in vacuo. To the obtained product was added ethyl acetate (400 mL) and the mixture was filtered. The filtrate was washed with water (100 mL), 1 N sodium hydroxide (2×50 mL), and brine (3×100 mL), dried (magnesium sulfate), and concentrated in vacuo to 37 g of ethyl 5-(4-formyl-3,5-dimethoxyphenoxy)valerate.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the obtained product was added ethyl acetate (400 mL)
  3. filtrationthe mixture was filtered
  4. washThe filtrate was washed with water (100 mL), 1 N sodium hydroxide (2×50 mL), and brine (3×100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo to 37 g of ethyl 5-(4-formyl-3,5-dimethoxyphenoxy)valerate

Sources & evidence

ORD record
ord-1cf60c876fbe4063b249ffb1131a01c0
Source dataset
uspto-grants-2005_09
Patent number
US06939880B2

Reaction notes

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