P-Cresol → HCID 54205510, compound

HRID 342412Notes

Reaction equation

HRID 342412 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4](Cl)=[O:5].[CH:12]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]([CH3:19])[CH:13]=1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([O:18][C:17]1[CH:12]=[CH:13][C:14]([CH3:19])=[CH:15][CH:16]=1)=[O:5]

Participants

5

Reactant 3

HCID 2879P-CresolHCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chloride

Product 1

HCID 54205510HCID 54205510, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Dichlorobenzoyl chloride (2.14 g) was added to a solution of p-cresol (1.08 g) and triethylamine (1.11 g) in dichloromethane (30 ml) dropwise at 4° C. The mixture was stirred at ambient temperature overnight. The reaction mixture was washed with aqueous saturated sodium bicarbonate and brine, dried over sodium sulfate and evaporated in vacuo to give 4-methylphenyl 2,6-dichlorobenzoate (2.73 g) as an oil. NMR (CDCl3, δ): 2.38 (3H, s), 7.17 (2H, d, J=8 Hz), 7.25 (2H, d, J=7 Hz), 7.30-7.45 (3H, m)

Workup

  1. washThe reaction mixture was washed with aqueous saturated sodium bicarbonate and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-2554357ec17546cda268a87f4bf19b0d
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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