Thionyl Chloride → HCID 10467905, compound

HRID 741909Notes

Reaction equation

HRID 741909 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][C:7]=1[O:15][CH3:16].S(Cl)([Cl:19])=O>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([Cl:19])=[O:11])=[CH:8][C:7]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10354496Benzoic acid, 4-(3-chloropropoxy)-3-methoxy-

Product 1

HCID 10467905HCID 10467905, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-(3-chloropropoxy)-3-methoxybenzoic acid (2.4 g, 10 mmol) in dichloromethane (5 ml) was added thionyl chloride (0.9 ml, 12 mmol) dissolved in dichloromethane (5 ml). The reaction was stirred and refluxed for 1 hour, and then the dichloromethane was removed in vacuo to leave a dark oil. The oil was triturated with hexane and the solid that formed while scratching with a glass rod was collected to afford 1.6 g of 4-(3-chloropropoxy)-3-methoxybenzoyl chloride, m.p.=60°-63° C.

Workup

  1. temperaturerefluxed for 1 hour
  2. customthe dichloromethane was removed in vacuo
  3. customto leave a dark oil
  4. customThe oil was triturated with hexane
  5. customthe solid that formed
  6. customwas collected

Sources & evidence

ORD record
ord-ec366da005c548b18127681cd07c9cfe
Source dataset
uspto-grants-1996_09
Patent number
US05552414

Reaction notes

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