Benzoyl chloride → 4-Benzyloxy-3-chloro-5-methyl-1-benzoyloxybenzene

HRID 363106Notes

Reaction equation

HRID 363106 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]=1[Cl:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([O:16][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:11][C:10]=1[Cl:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 185046314-Benzyloxy-3-chloro-5-methylphenol

Product 1

HCID 185045544-Benzyloxy-3-chloro-5-methyl-1-benzoyloxybenzeneYield 90.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 27.3 g of 4-benzyloxy-3-chloro-5-methylphenol dissolved in 250 ml of chloroform and stirred at 0° C. were added 15.4 g of benzoyl chloride and then 13.3 g of triethylamine. After stirring at room temperature for 2 hours, the chloroform layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel chromatography, which afforded 35 g of 4-benzyloxy-3-chloro-5-methyl-1-benzoyloxybenzene (90% yield).

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. washthe chloroform layer was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8eb169f2080549fd9d816b7da9a110ca
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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