Toluene → 1-(3,5-Dimethoxyphenyl)-2-(4-isopropyloxyphenyl)ethanone

HRID 424031Notes

Reaction equation

B(O)(O)O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15](=[O:31])[CH:16]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH:28]([CH3:30])[CH3:29])=[CH:23][CH:22]=2)C(OC)=O)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1.C1(C)C=CC=CC=1>O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15](=[O:31])[CH2:16][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH:28]([CH3:29])[CH3:30])=[CH:25][CH:26]=2)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1

Participants

Conditions

Temperature: 152.5 °C

Procedure

9.65 g of boric acid (0.16 mol) and 58 g of crude methyl 3-(3,5-dimethoxyphenyl)-2-(4-isopropyloxyphenyl)-3-oxopropionate (0.16 mol) prepared according to Example 25 are introduced into a round-bottomed flask. The mixture is heated with stirring at 150-155° C. for 3 h and then cooled to approximately 80° C. 200 ml of toluene and then 150 ml of water are added. Separation by settling is carried out and the organic phase is recovered. The aqueous phase is re-extracted with 20 ml of toluene. The organic phases are concentrated to recover 48.8 g of crude 1-(3,5-dimethoxyphenyl)-2-(4-isopropyloxyphenyl)ethanone in the form of a viscous oil with a dark brown color.

Workup

additionare introduced into a round-bottomed flask
temperatureThe mixture is heated
temperaturecooled to approximately 80° C
customSeparation
customthe organic phase is recovered
extractionThe aqueous phase is re-extracted with 20 ml of toluene
concentrationThe organic phases are concentrated
customto recover 48.8 g of crude 1-(3,5-dimethoxyphenyl)-2-(4-isopropyloxyphenyl)ethanone in the form of a viscous oil with a dark brown color

Sources & evidence

ORD record: ord-f83aadee276f406cadbf61662712b394
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101804B2

Reaction notes

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