3-Chlorophenol → HCID 570499, compound

HRID 1866810Notes

Reaction equation

HRID 1866810 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:25])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][C:16](=[O:25])[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 8471TriethylamineHCID 64801Benzenepropanoyl chloride

Product 1

HCID 570499HCID 570499, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chlorophenol (1, 50.1 g, 0.3 mol), triethylamine (TEA, 85 mL), and CH2Cl2 (500 mL) at 23° C. was added hydrocinnamoyl chloride (2, 31 mL, 0.3 mol) over 5 minutes. After 30 minutes, the reaction mixture was concentrated in vacuo. The crude slurry was then dissolved in 10:1 hexanes:EtOAc (300 mL) and washed with 1 N NaOH (100 mL) and brine (100 mL). The organic layer was dried (MgSO4) and filtered through a plug of silica gel (10:1 hexanes:EtOAc rinse). The eluent was concentrated to afford 78 g of a slightly yellow oil, which was used without any further purification.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe crude slurry was then dissolved in 10:1 hexanes
  3. washEtOAc (300 mL) and washed with 1 N NaOH (100 mL) and brine (100 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered through a plug of silica gel (10:1 hexanes:EtOAc rinse)
  6. concentrationThe eluent was concentrated
  7. customto afford 78 g of a slightly yellow oil, which
  8. customwas used without any further purification

Sources & evidence

ORD record
ord-b1c5a5eaa6154b13b19a65791616e09b
Source dataset
uspto-grants-2009_12
Patent number
US07629477B2

Reaction notes

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