Ethanol → Ethyl (3-Hydroxyphenyl)acetate

HRID 1820937Notes

Reaction equation

HRID 1820937 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH:12]1(N=C=NC2CCCCC2)CCCC[CH2:13]1.N1C=CC=CC=1.C(O)C>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 572437Ethyl (3-Hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-Hydroxyphenylacetic acid (10 g, 65.7 mmol) and 1,3-dicyclohexylcarbodiimide (DCC, 16.27 g, 78.8 mmol) in DMF (30 ml) was added pyridine (2.5 ml) followed by absolute ethanol (15 ml, 255.5 mmol). The reaction mixture was stirred at room temperature for 16 hours, filtered, concentrated and purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1) to give the title compound.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-f925166d56a847e7bc1dec9e1961ddc5
Source dataset
uspto-grants-2009_10
Patent number
US07605181B2

Reaction notes

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