2-Chloroethanol → 2-Chloroethyl 3-hydroxybenzoate

HRID 2392967Notes

Reaction equation

HRID 2392967 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Cl:11][CH2:12][CH2:13]O>OS(O)(=O)=O.O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:13][CH2:12][Cl:11])=[O:6]

Participants

5

Reactant 2

HCID 342-ChloroethanolHCID 74203-Hydroxybenzoic Acid

Product 1

HCID 151587912-Chloroethyl 3-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 65 g of 3-hydroxybenzoic acid (0.47 mol) in 500 mL of 2-chloroethanol and 3 mL of H2SO4 was refluxed for 4 hours. The cooled solution was diluted with 500 mL of water and extracted with ethyl acetate (3×250 mL). The ethyl acetate was extracted twice with aqueous NaHCO3 and then with water. The ethyl acetate solution was dried and evaporated under reduced pressure yielding 85 g of product as a thick oil; 1H NMR (CDCl3) δ3.814 (t,2H, J=6 Hz), 4.569 (t,2H, J=6 Hz), 5.36 (br s,1H), 7.06-7.67 (m,4H). ##STR12##

Workup

  1. extractionextracted with ethyl acetate (3×250 mL)
  2. extractionThe ethyl acetate was extracted twice with aqueous NaHCO3
  3. dry with materialThe ethyl acetate solution was dried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4145b6a6da614719bd9c784ff5ccd77d
Source dataset
uspto-grants-1998_09
Patent number
US05804103

Reaction notes

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