Ethanol → Ethyl 2-(2-ethoxy-4-formylphenoxy)acetate

HRID 1503634Notes

Reaction equation

HRID 1503634 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Br)[CH3:20].C(O)C>CC(C)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]=[O:8])[CH:9]=[CH:10][C:11]=1[O:12][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 8467EthylvanillinHCID 11430Potassium Carbonate

Product 1

HCID 880082Ethyl 2-(2-ethoxy-4-formylphenoxy)acetateYield 63.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound was prepared according to general procedure E with 3-ethoxy-4-hydroxybenzaldehyde (2.4 mmol) in dry acetone (15 ml), anhydrous K2CO3 (3.1 mmol), and ethylbromoacetate (3.6 mmol) at reflux for 1 h30. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate. 565 mg of crude product were obtained and purified by silica gel chromatography (eluent dichloromethane). 385 mg of purified compound were obtained (63% yield). 1H NMR (250 MHz, CDCl3): δ 1.31 (t, J=7.0 Hz, 3H), 1.49 (t, J=7.0 Hz, 3H), 4.18 (q, J=7.0 Hz, 2H), 4.31 (q, J=7.0 Hz, 2H), 4.79 (s, 2H), 6.91 (d, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.45 (s, 1H) 9.86 (s, 1H) 13C NMR (63 MHz, CDCl3): δ 14.0, 14.5, 61.2, 64.4, 65.9, 111.2, 113.0, 125.5, 131.0, 149.1, 152.7, 168.1, 191.5. MS (ESI): m/z 253.0 [M+H]+.

Workup

  1. customThe compound was prepared
  2. temperatureat reflux for 1 h30
  3. customevaporated by azeotropic distillation with ethylbromoacetate
  4. custom565 mg of crude product were obtained
  5. custompurified by silica gel chromatography (eluent dichloromethane)

Sources & evidence

ORD record
ord-58523edf728746dbb1caec96a52ac10c
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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