Ethyl 4-hydroxyphenylacetate → Ethyl 3-chloro-4-hydroxyphenylacetate

HRID 446825Notes

Reaction equation

HRID 446825 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C1C(=O)N([Cl:21])C(=O)C1>C1COCC1>[Cl:21][C:7]1[CH:6]=[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 28310Ethyl 4-hydroxyphenylacetateHCID 31398Chlorosuccinimide

Product 1

HCID 11031224Ethyl 3-chloro-4-hydroxyphenylacetateYield 116.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of ethyl 2-(4-hydroxyphenyl)acetate (5.0 g, 0.02 mol) in THF (100 mL) was added NCS (4.45 g, 0.03 mol). The reaction mixture was then stirred at RT for 16 h and then extracted with EtOAc (2×200 mL). The combined organic layers were washed with water, dried over Na2SO4, and concentrated in vacuo to afford ethyl 2-(3-chloro-4-hydroxyphenyl)acetate (5 g, 84%) as a solid.

Workup

  1. extractionextracted with EtOAc (2×200 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13d2883cdca440ea932d2827a5afb064
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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