Water → Ethyl 2-(3-formylphenoxy)acetate

HRID 592073Notes

Reaction equation

HRID 592073 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][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 1317345403-Hydroxy benzaldehyde ethyl 2-bromoacetate

Product 1

HCID 1494377Ethyl 2-(3-formylphenoxy)acetateYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-hydroxy benzaldehyde/ethyl 2-bromoacetate (1.1 eq) and K2CO3 (2 eq) were taken in DMF and heated at 80° C. for 16 h when TLC indicated completion of reaction. The reaction mixture was cooled to rt and poured into water. Extraction was done with DCM. The combined organic extracts was dried, concentrated and purified by column chromatography using silica gel (100-200 mesh) to afford the pure product (23%) as a colorless oil. NMR: δ 1.298 (t, J=7.2 Hz, 3H), 4.27 (q, J=7.2 Hz, 2H), 4.683 (s, 1H), 7.20-7.27 (m, 1H), 7.361 (s, 1H), 7.42-7.52 (m, 2H), 9.96 (s, 1H).

Workup

  1. customcompletion of reaction
  2. temperatureThe reaction mixture was cooled to rt
  3. extractionExtraction
  4. customThe combined organic extracts was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-c91c6ea9d1bf47858af8a512b83cc93f
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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