4-Hydroxybenzaldehyde → Ethyl 2-(4-formylphenoxy)propionate

HRID 1503637Notes

Reaction equation

HRID 1503637 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16]([O:18][C:19](=[O:23])[CH:20](Br)[CH3:21])[CH3:17].C(O)(C)C>CC(C)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH:20]([CH3:21])[C:19]([O:18][CH2:16][CH3:17])=[O:23])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 3016639Ethyl 2-(4-formylphenoxy)propionateYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound was prepared according to general procedure E with 4-hydroxybenzaldehyde (3.3 mmol) in dry acetone (15 ml), anhydrous K2CO3 (4.3 mmol), and ethyl-2 bromopropionate (3.6 mmol) at reflux for 2 h45. Isopropanol was added and evaporated by azeotropic distillation with ethyl-2-bromopropionate. 609 mg of pure compound were obtained (83% yield). 1H NMR (250 MHz, CDCl3): δ 1.10 (t, J=7.1 Hz, 3H), 1.52 (d, J=6.8 Hz, 3H), 4.10 (q, J=7.1 Hz, 2H), 4.76 (q, J=6.8 Hz, 1H) 6.85 (d, J=8.7 Hz 2H), 7.70 (d, J=8.9 Hz, 2H), 9.74 (s, 1H) 13C NMR (63 MHz, CDCl3): δ 14.0, 18.2, 61.4, 72.4, 115.1, 130.4, 131.8, 162.4, 171.1, 190.5

Workup

  1. customThe compound was prepared
  2. temperatureat reflux for 2 h45
  3. customevaporated by azeotropic distillation with ethyl-2-bromopropionate

Sources & evidence

ORD record
ord-85d9a296504b40d3b063d04e3a7ee684
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

Loading…