Diethyl Ether → Ethyl 3-chloro-4-hydroxyphenylacetate

HRID 385442Notes

Reaction equation

HRID 385442 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.S(Cl)([Cl:17])(=O)=O.C(OCC)C>C(Cl)Cl>[Cl:17][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 3283Diethyl EtherHCID 24648Sulfuryl chlorideHCID 28310Ethyl 4-hydroxyphenylacetate

Product 1

HCID 11031224Ethyl 3-chloro-4-hydroxyphenylacetateYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
15 °C

Procedure

To a stirred solution of ethyl 2-(4-hydroxyphenyl)acetate (25 g, 138 mmol) in 375 ml of DCM, sulfuryl chloride (9.48 mL 118 mmol) was slowly added at 0° C. over a period of 30 min. Diethyl ether (19.6 mL) was slowly added reaction mixture at 0° C. and stirring was continued for 30 min at 0° C. The reaction mixture was slowly warmed to 15° C. for 1 h. After completion of reaction, the mixture was poured onto crushed ice and extracted with DCM (×2). The combined organic layers were washed with 10% NaHCO3 solution followed by water. The organic layer was dried over Na2SO4, filtered and evaporated under vacuum to give compound ethyl 2-(3-chloro-4-hydroxyphenyl)acetate (15 g) as a thick oil.

Workup

  1. customreaction mixture at 0° C.
  2. customAfter completion of reaction
  3. additionthe mixture was poured
  4. customonto crushed ice
  5. extractionextracted with DCM (×2)
  6. washThe combined organic layers were washed with 10% NaHCO3 solution
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-485475320eee40bf8bfcba4c319b3988
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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