Sulfuryl chloride → HCID 68768481, compound

HRID 587823Notes

Reaction equation

HRID 587823 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[CH3:2].S(Cl)([Cl:18])(=O)=O>C(OCC)C>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][C:12]=1[Cl:18])[CH3:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 15197885Ethyl 3-(3-hydroxyphenyl)propanoate

Product 1

HCID 68768481HCID 68768481, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0° C. solution of 3-(3-hydroxy-phenyl)-propionic acid ethyl ester (1.0 g, 5.15 mmol) in diethyl ether (50 ml) was added sulfuryl chloride (0.493 mL, 6.18 mmol). After 2.5 h at 0° C., the reaction was quenched with sat. sodium carbonate (50 ml). The aqueous layer was extracted with ethyl acetate. The organic portions were combined and dried with magnesium sulfate. The solvent was removed in vacuo to afford crude product, which was purified by column chromatography (10% ethyl acetate/hexanes). The title compound was obtained as colorless oil (0.73 g, yield 62%): 1H NMR (CDCl3) δ 6.96 (d, J=10.1 Hz, 1H); 6.54 (d, J=2.97 Hz, 1H); 6.46 (dd, J=8.6, 3.0 Hz, 1H); 3.96 (dd, J=12.5 5.3 Hz, 2H); 2.82-2.78 (m, 2H); 1.08-1.00 (m, 3H).

Workup

  1. customthe reaction was quenched with sat. sodium carbonate (50 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customto afford crude product, which
  6. customwas purified by column chromatography (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f16aa1f5564249f6b386ca3235fd7162
Source dataset
uspto-grants-2016_01
Patent number
US09227914B2

Reaction notes

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