Ethanol → Ethyl (4-formyl-2-methoxyphenoxy)acetate

HRID 1503636Notes

Reaction equation

HRID 1503636 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Br)[CH3:19].C(O)C>CC(C)=O>[CH:2]([C:3]1[CH:11]=[CH:10][C:8]([O:9][CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:24])=[C:5]([O:6][CH3:7])[CH:4]=1)=[O:1]

Participants

6

Reactant 4

HCID 702EthanolHCID 1183VanillinHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 968872Ethyl (4-formyl-2-methoxyphenoxy)acetateYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound was prepared according to general procedure E with vanillin (5.3 mmol) in dry acetone (20 ml), anhydrous K2CO3 (6.8 mmol), and ethylbromoacetate (6.3 mmol) at reflux for 1 h. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate. 980 mg of pure compound were obtained (78% yield). 1H NMR (250 MHz, CDCl3): δ 1.23 (m, 3H), 3.88 (s, 3H), 4.21 (m, 2H), 4.78 (s, 2H), 6.90 (m, 1H), 7.38 (m 2H), 9.80 (s, 1H) 13C NMR (63 MHz, CDCl3): δ 13.9, 55.7, 61.2, 65.6, 109.8, 112.3, 125.7, 130.8, 149.7, 152.4, 167.9, 190.6 MS (ESI): m/z 253.0 [M+H]+.

Workup

  1. customThe compound was prepared
  2. temperatureat reflux for 1 h
  3. customevaporated by azeotropic distillation with ethylbromoacetate

Sources & evidence

ORD record
ord-c9040b5e4ee34812934607e329be512d
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

Loading…