Oxalyl chloride → HCID 22323720, compound

HRID 324250Notes

Reaction equation

HRID 324250 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-

Product 1

HCID 22323720HCID 22323720, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 3-(4-methoxy-pbenylsulfanyl)-3methyl-butyric acid (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 mi of benzene over 30 minutes. After 4 h, 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 (3(4-methoxy-phenylsulfanyl)3-methyl-butyroyl chloride) was used without further purification in the next step. 1H NMR (300 MHz, CDCl3) δ: 7.45 (2H, d, J=8.8 Hz), 3.84 (3H, s), 3.12 (2H, s, 1.41 (6H, s).

Workup

  1. washthe 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 (3(4-methoxy-phenylsulfanyl)3-methyl-butyroyl chloride) was used without further purification in the next step

Sources & evidence

ORD record
ord-89cebc36228a49b1abaefd9b50ac60b5
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

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