Toluene → [4-(2-Hydroxyethoxy)phenyl](phenyl)methanone

HRID 1525622Notes

Reaction equation

[C:1]1(=O)[O:5][CH2:4][CH2:3][O:2]1.O[C:8]1[CH:21]=[CH:20][C:11]([C:12]([C:14]2[CH:19]=[CH:18]C=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1.C1(C)C=CC=CC=1>[I-].[Na+].C1(C)C=CC=CC=1.O>[OH:2][CH2:3][CH2:4][O:5][C:1]1[CH:18]=[CH:19][C:14]([C:12]([C:11]2[CH:20]=[CH:21][CH:8]=[CH:9][CH:10]=2)=[O:13])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 176 °C

Procedure

A mixture of ethylene carbonate (124.6 g; 1.07 eq.), sodium iodide (6.3 g; 0.03 eq.), 4-hydroxybenzophenone (262 g; 1 eq.) and toluene (8.1 g) was heated. At 99° C. a clear solution was obtained. The reaction mixture was heated with reflux condenser to 176° C. over one hour, during which gas evolution occurred. After an additional ½ hour at 176° C., the reaction mixture was cooled to 122° C. and toluene (350 g) and water (24 g) was added. The lower phase was cut and discarded. More water (14 g) was added and the lower phase was again cut and discarded. Water and toluene (95 g in total) was azeotropically removed, reaching a boiling point of 111° C. More toluene (114 g) was added and the product was isolated by filtration at 8° C. In total, 302 g of 4-(2-hydroxyethoxy)benzophenone (94%) was obtained after drying as white crystals (99.8% chromatographic purity).

Workup

temperaturewas heated
customAt 99° C. a clear solution was obtained
temperatureThe reaction mixture was heated
temperaturethe reaction mixture was cooled to 122° C.
customWater and toluene (95 g in total) was azeotropically removed
additionMore toluene (114 g) was added
customthe product was isolated by filtration at 8° C

Sources & evidence

ORD record: ord-d7ac48633c8245a58c8ba70a87db95ce
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085519B2

Reaction notes

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