Hydroquinone → 4-(4-Hydroxy-phenoxy)-butyric acid ethyl ester

HRID 2361933Notes

Reaction equation

HRID 2361933 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 189185904-(4-Hydroxy-phenoxy)-butyric acid ethyl esterYield 30%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-hydroxyphenol (3.3 g, 30 mmol) in ethanol (60 mL) was added K2CO3 (6.21 g, 45 mmol), Bu4NI (1.11 g, 3 mmol), and ethyl 4-bromobutanoate (4.68 g, 24 mmol). The resulting mixture was stirred at 60° C. overnight and filtered. To the filtrate was added water, and extracted with ethyl acetate, washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford title product 0112-54 (1.6 g, 30%) as a brown solid. LCMS: 247 [M+23]+. 1H NMR (400 MHz, DMSO-d6): δ 1.26 (t, J=7.2 Hz, 3H), 2.08 (m, 2H), 2.51 (t, J=7.2 Hz, 2H), 3.93 (t, J=6.0 Hz, 2H), 4.15 (q, J=7.2 Hz, 2H), 6.75 (s, 4H).

Workup

  1. filtrationfiltered
  2. additionTo the filtrate was added water
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10% v/v)

Sources & evidence

ORD record
ord-544f46f91ab744008827a6d9b98bd2d3
Source dataset
uspto-grants-2014_04
Patent number
US08691820B2

Reaction notes

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