Thionyl Chloride → HCID 22381862, compound

HRID 1835131Notes

Reaction equation

HRID 1835131 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])[CH2:2][CH3:3].[Cl:14][S:15](O)(=[O:17])=[O:16].S(Cl)(Cl)=O>C(Cl)Cl>[Cl:14][S:15]([C:11]1[CH:12]=[CH:13][C:5]([O:4][CH2:1][CH2:2][CH3:3])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 5392152-Propoxybenzoic acid

Product 1

HCID 22381862HCID 22381862, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 2-n-propoxybenzoic acid (20 g, 111 mmol) in DCM (40 ml) was added dropwise over 30 min to a mixture of chlorosulphonic acid (30 ml, 440 mmol) and thionyl chloride (8.1 ml, 110 mmol) at −10° C. whilst keeping the temperature below 0° C. The mixture was slowly warmed to 20° C. and stirred for 18 h. The reaction mixture was cautiously poured onto crushed ice (260 g), keeping the temperature below 0° C. The ice slurry was stirred for 20 min and then the precipitated white solid was filtered, washed with H2O (20 ml), dissolved in DCM (200 ml), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a yellow solid (31.2 g, 103 mmol, 92%); mp 121-124° C.

Workup

  1. customthe temperature below 0° C
  2. additionThe reaction mixture was cautiously poured
  3. customthe temperature below 0° C
  4. filtrationthe precipitated white solid was filtered
  5. washwashed with H2O (20 ml)
  6. dissolutiondissolved in DCM (200 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ecba102d081647b180ea16753a52910f
Source dataset
uspto-grants-2004_08
Patent number
US06770645B2

Reaction notes

Loading…