Benzoyl chloride → 4-Benzyloxy-3-ethyl-5-methylphenyl benzoate

HRID 369683Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]=1[CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)(Cl)Cl>[C:26]([O:16][C:12]1[CH:13]=[C:14]([CH3:15])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH2:17][CH3:18])[CH:11]=1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 6.3 g of 4-benzyloxy-3-ethyl-5-methylphenol, 3.2 g of triethylamine and 50 ml of chloroform was added dropwise 4.0 g of benzoyl chloride with stirring at 0° C. After stirring at room temperature for 6 hours, the reaction mixture was concentrated under reduced pressure. To the residue was added 100 ml of 10% hydrochloric acid, which was extracted with 100 ml of ethyl acetate. The ethyl acetate layer was washed with 10% hydrochloric acid, aqueous sodium hydrogencarbonate solution and then saturated sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, which afforded 8.4 g of crude 4-benzyloxy-3-ethyl-5-methylphenyl benzoate (yield, 93%).

Workup

stirringAfter stirring at room temperature for 6 hours
concentrationthe reaction mixture was concentrated under reduced pressure
additionTo the residue was added 100 ml of 10% hydrochloric acid, which
extractionwas extracted with 100 ml of ethyl acetate
washThe ethyl acetate layer was washed with 10% hydrochloric acid, aqueous sodium hydrogencarbonate solution
dry with materialsaturated sodium chloride solution, dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure, which

Sources & evidence

ORD record: ord-3bd233dbe9904109b7a81ed38e5f9117
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06140274

Reaction notes

Loading…