3-Hydroxybenzaldehyde → Ethyl 2-(3-formylphenoxy)acetate

HRID 929644Notes

Reaction equation

HRID 929644 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>O1CCCC1>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 1494377Ethyl 2-(3-formylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxybenzaldehyde (2.00 g, 16.4 mmol) was dissolved in 25 mL of dry tetrahydrofuran under nitrogen with 3.5 g of potassium carbonate and 3.01 g (18.0 mmol) of ethyl bromoacetate. The reaction was heated at reflux for 6 hr, then cooled to room temperature and filtered from inorganic salts. The filtrate was evaporated, redissolved in 30 mL of methylene chloride, washed with 2×15 mL of water, and dried over sodium sulfate. Evaporation of solvent gave 2.92 of ethyl 3-formylphenoxyacetate as a yellow oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 6 hr
  3. filtrationfiltered from inorganic salts
  4. customThe filtrate was evaporated
  5. dissolutionredissolved in 30 mL of methylene chloride
  6. washwashed with 2×15 mL of water
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of solvent

Sources & evidence

ORD record
ord-d087d6a089fe42b5ab7d3e1dcb68a2fa
Source dataset
uspto-grants-2016_03
Patent number
US09296707B2

Reaction notes

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