Sulfuryl chloride → Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-phenoxypropionate

HRID 1860093Notes

Reaction equation

HRID 1860093 reaction equation
S(Cl)([Cl:4])(=O)=O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1>C(OCC)C>[Cl:4][C:12]1[CH:11]=[C:10]([CH2:13][CH:14]([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:8][C:7]=1[OH:6]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 18625748Ethyl 3-(4-hydroxyphenyl)-2-phenoxypropionate

Product 1

HCID 18625720Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-phenoxypropionate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of sulfuryl chloride (0.71 ml) in diethyl ether (5 ml) was added dropwise to a solution of ethyl 3-(4-hydroxyphenyl)-2-phenoxypropionate (1.43 g) in diethyl ether (20 ml) at ambient temperature. The mixture was stirred for 8 hour and allowed to stand overnight. The reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=10/3 as the eluant to afford the desired compound (1.09 g) as a colorless oil.

Workup

  1. waitto stand overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-704fa848ee754d43a301f48797d18df4
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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