Catechol → Ethyl 4-(2-hydroxyphenoxy)butanoate

HRID 40813Notes

Reaction equation

HRID 40813 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[H-].[Na+].Br[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C=O)C>[OH:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 289CatecholHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 15887568Ethyl 4-(2-hydroxyphenoxy)butanoateYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of pyrocatechol (5.51 g, 50 mmol) in dry DMF (30 mL) was slowly added sodium hydride (1.2 g, 50 mmol) at 0° C. After stirring at 25° C. for 4 hours, the reaction mixture was heated at 65-70° C. for 1 hour followed by an addition of ethyl 4-bromobutyrate (10.7 mL, 75 mmol). The reaction mixture was then left stirring at this temperature for 6 hours. Upon quenching with water, extraction with dichloromethane, and evaporation gave the crude product which was purified by column chromatography, eluting with 87% hexane:10% CH2Cl2:3% EtOAc. Crystallization with hexane afforded a white solid in 55% yield (6.17 g, mp. 37.2-38.4° C.). 1H NMR (400 MHz, CDCl3): 1.26 (3H, t, J=7.1 Hz), 2.17 (2H, m), 2.52 (2H, t, J=7.0 Hz), 4.09 (2H, t, J=6.0 Hz), 4.16 (2H, q, J=7.1 Hz), 6.81-6.89 (3H, m), 6.92-6.94 (1H, m).

Workup

  1. customat 0° C
  2. temperaturethe reaction mixture was heated at 65-70° C. for 1 hour
  3. waitThe reaction mixture was then left
  4. stirringstirring at this temperature for 6 hours
  5. customUpon quenching with water, extraction with dichloromethane, and evaporation

Sources & evidence

ORD record
ord-2060026c597745bbb4a940326ca3d102
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

Loading…