Thionyl Chloride → HCID 10467905, compound

HRID 744493Notes

Reaction equation

HRID 744493 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 for1 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 for1 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-8b6c79b140884c10b029128dde4b153b
Source dataset
uspto-grants-1996_09
Patent number
US05559126

Reaction notes

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