Oxalyl chloride → HCID 22323720, compound

HRID 619617Notes

Reaction equation

HRID 619617 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([CH3:16])([CH3:15])[CH2:11][C:12](O)=[O:13])=[CH:5][CH:4]=1.C(Cl)(=O)C([Cl:20])=O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([CH3:16])([CH3:15])[CH2:11][C:12]([Cl:20])=[O:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 10171427Butanoic acid, 3-[(4-methoxyphenyl)thio]-3-methyl-2×

Product 1

HCID 22323720HCID 22323720, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 3-(4-methoxy-phenylsulfanyl)-3-methyl-butyric acid (Compound 216, 20.0 g, 83.2 mmol) in 250 mL of benzene at room temperature was added a solution of oxalyl chloride (15.84 g, 124.8 mmol) in 10 mL of benzene over 30 minutes. After 4 hours the solution was washed with ice cold 5% aqueous NaOH (CAUTION: a large volume of gas is released during this procedure), followed by ice cold H2O, and finally saturated aqueous NaCl. The solution was dried (Na2SO4) and concentrated under reduced pressure to give a clear yellow oil. This material was used without further purification in the next step. 1H NMR (300 MHz, CDCl3) δ: 7.45 (2H, d, J=8.8 Hz), 6.90 (2H, d, J=8.8 Hz), 3.84 (3H, s), 3.12 (2H, s), 1.41 (6H, s).

Workup

  1. washAfter 4 hours the solution was washed with ice cold 5% aqueous NaOH (CAUTION
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give a clear yellow oil
  5. customThis material was used without further purification in the next step

Sources & evidence

ORD record
ord-6310125a2d7f41078b120e7fd76a466e
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

Loading…