2,6-Di-tert-butylphenol → 4-(2-Chloronicotinoyl)2,6-di-tertiary butylphenol

HRID 1382873Notes

Reaction equation

HRID 1382873 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:16]=1[OH:25])([CH3:14])([CH3:13])[CH3:12]>ClC(Cl)C>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([C:19]1[CH:18]=[C:17]([C:21]([CH3:22])([CH3:23])[CH3:24])[C:16]([OH:25])=[C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:20]=1)=[O:5]

Participants

4

Reactant 2

HCID 314052,6-Di-tert-butylphenolHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 143682724-(2-Chloronicotinoyl)2,6-di-tertiary butylphenolYield 79.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of 282 g of 2-chloronicotinoyl chloride and 400 g of 2,6-di-tertiary butylphenol in 1000 ml of dichloroethane under ice-cooling is added dropwise a solution of 500 g of anhydrous stannic chloride in 250 ml of dichloroethane with stirring over 50 minutes. The reaction temperature is kept below 5° C. during the addition. After completion of the addition, the mixture is stirred at room temperature for 1.5 hours. The resulting reaction mixture is poured into ice-cold water and stirred for a while. The organic layer is separated, washed with water, dried and then concentrated. The obtained residue is recrystallized from an aqueous solution of 80% methanol to give 442 g of 4-(2-chloronicotinoyl)-2,6-di-tertiary butylphenol as pale yellow crystals, melting at 135°-137° C.

Workup

  1. additionThe reaction temperature is kept below 5° C. during the addition
  2. additionAfter completion of the addition
  3. stirringthe mixture is stirred at room temperature for 1.5 hours
  4. customThe resulting reaction mixture
  5. additionis poured into ice-cold water
  6. stirringstirred for a while
  7. customThe organic layer is separated
  8. washwashed with water
  9. customdried
  10. concentrationconcentrated
  11. customThe obtained residue is recrystallized from an aqueous solution of 80% methanol

Sources & evidence

ORD record
ord-847f012301874e42b334383c85ece338
Source dataset
uspto-grants-1989_02
Patent number
US04808620

Reaction notes

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