Phenol → Acetic acid, 2-phenoxy-, ethyl ester

HRID 1053526Notes

Reaction equation

HRID 1053526 reaction equation
BrCCCOC1C=CC=CC=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>>[O:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 996PhenolHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-

Product 1

HCID 17365Acetic acid, 2-phenoxy-, ethyl esterYield 81%

Procedure

The compound 34 was prepared according to the method described for compound 26 employing phenol (4.5 g, 0.05 mol), ethyl bromoacetate (31 g, 0.19 mol) and potassium carbonate (33 g, 0.24 mol) to give a colorless oily compound 34 (6.9 g, 81%). 1H NMR (300 MHz, CD2Cl2) δ 1.30 (t, J=7.0 Hz, 3H), 4.27 (q, J=7.0 Hz, 2H), 4.62 (s, 2H), 6.91 (d, J=7.9 Hz, 2H), 6.99 (t, J=7.0 Hz, 1H), 7.29 (t, J=7.6 Hz, 2H).

Workup

  1. customThe compound 34 was prepared

Sources & evidence

ORD record
ord-05ad2179c9264d338fe34cf27763b7e9
Source dataset
uspto-grants-2016_07
Patent number
US09393306B2

Reaction notes

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