3,5-Dibenzyloxyacetophenone

English synonyms

3,5-DIBENZYLOXYACETOPHENONE;3',5'-DIBENZYLOXYACETPHENONE;
3',5'-BIS(BENZYLOXY)ACETOPHENONE;1-[3,5-bis(phenylmethoxy)phenyl]-ethanon;
1-[3,5-BChemicalbookis(benzyloxy)phenyl]ethan-1-one;TerbutalineImpurity1;

3',5'-Dibenzyloxyacetophenone3,5-Dibenzyloxyacetophenone;

(3,5-BIS-BENZYLOXY-PHENYL)-METHANOL

CAS number

28924-21-2

Molecular formula

C22H20O3

Molecular weight

332.39

EINECS number

249-315-7

Melting point

60-62℃(lit.)

Boiling point

429.52℃(rough estimate)

Density

1.1079(rough estimate)

Refractive index

1.6000(estimate)

Storage conditions

Sealed in dry,Room Temperature

Solubility

Soluble in dichloromethane, ethyl acetate and methanol

Form

Solid

Color

Off-white to light yellow

InChlKey

KOJXGMJOTRYLBD-UHFFFAOYSA-N

CAS database

28924-21-2(CAS DataBase Reference)

EPA chemical information

Ethanone,1-[3,5-bis(phenylmethoxy)phenyl]-(28924-21-2)

Uses

3,5-Dibenzyloxyacetophenone is widely used as an intermediate in the production of drugs for the treatment of obesity,
diabetes,glaucoma, AIDS, HIV infection, anti-inflammatory effects, and is also used to treat diseases caused by leukotrienes,
sedatives,antihypertensive drugs, diuretics and anti-glaucoma drugs.

Preparation method

Methyl lithium (531 mL of a 2 molar solution, 1.06 M) was added to a rapidly stirred solution of 3,5-dibenzyloxybenzoic
acid (175 g, 0.532 M) in ether (250 mL) and tetrahydrofuran (1400 mL) over 1.5 hours under a nitrogen atmosphere. After stirring
at 10°-15°C for another 0.75 hours, water (600 mL) was slowly added, keeping the reaction temperature below 20°C. The aqueous layer
was separated and extracted with ether (3×250 mL).The organic phases were combined,washed with saturated sodium chloride
solution (4×300 ml), dried over sodium sulfate, and concentrated in vacuo to give an oil that slowly crystallized from isopropyl ether.
The crude product was recrystallized from ether-hexane to give 104.7 g. (59%)3,5-dibenzyloxyacetophenone; melting point 59°-61°C.

Chemical properties

Off-white crystalline powder, a compound useful in organic synthesis.

Hazardous Materials Sign

Xi

Safety Instructions

24/25

WGK Germany

3

Hazard Note

Irritant

TSCA

Yes

Customs Code

29145090

Upstream raw materials

3,5-Dibenzyloxybenzoic acid, terbutaline impurities, benzyl chloride, benzyl bromide

Downstream products

3,5-Dihydroxyacetophenone, 1-chloro-3-ethoxypropane, terbutaline