Methanol → Ethyl 3-chloro-4-hydroxyphenylacetate

HRID 385373Notes

Reaction equation

HRID 385373 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.CO.S(Cl)([Cl:19])(=O)=O>C(Cl)Cl>[Cl:19][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

5

Reactant 3

HCID 887MethanolHCID 24648Sulfuryl chlorideHCID 28310Ethyl 4-hydroxyphenylacetate

Product 1

HCID 11031224Ethyl 3-chloro-4-hydroxyphenylacetateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of ethyl 2-(4-hydroxyphenyl)acetate (20 g, 0.076 molo) in 200 ml of DCM was added MeOH (3.4 ml, 0.84 mol). The mixture was brought to reflux and sulfuryl chloride (6.8 ml 0.846 mol) dissolved in DCM (50 mL) was slowly added under over 10 min. The reaction mixture was refluxed further for 5 h, upon which the reaction mixture was poured onto crushed ice and extracted with DCM (×2). The combined organic layers were washed with 10% NaHCO3 solution and water. The organic layer was dried over Na2SO4, filtered and evaporated under vacuum to give compound ethyl 2-(3-chloro-4-hydroxyphenyl)acetate in 60% yield. (13.6 g).

Workup

  1. temperatureto reflux
  2. additionwas slowly added under over 10 min
  3. temperatureThe reaction mixture was refluxed further for 5 h, upon which the reaction mixture
  4. additionwas poured
  5. customonto crushed ice
  6. extractionextracted with DCM (×2)
  7. washThe combined organic layers were washed with 10% NaHCO3 solution and water
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-b9fbedd8701a4df6bab4e2ccb17030a6
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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