4-(2',3'-Dimethoxyphenyl) 3-phenylbutyric acid → 5,6-Dimethoxy-3-phenyl-3,4-dihydronaphthalen-1(2H)-one

HRID 54118

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][C:14](O)=[O:15]>O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]2[C:4]=1[CH2:11][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][C:14]2=[O:15]

Participants

Conditions

Temperature: 100 °C

Procedure

4-(2',3'-Dimethoxyphenyl)-3-phenylbutyric acid (37 g, 123 mmol), from Step 5, was added dropwise to 200 g of polyphosphoric acid heated to 100° C. The resultant mixture was stirred and heated at 100° C. for 0.25 h. A mixture of 100 g of ice and 200 mL of water was added to the reaction mixture. The precipitate which formed was filtered, washed with 3×75 mL of water and dissolved in 300 mL of methylene chloride. The methylene chloride solution was dried over anhydrous magnesium sulfate, filtered and concentrated to give 28 g (81% yield) of 5,6-dimethoxy-3-phenyl-1,2,3,4-tetrahydronaphthalen-1-one, m.p; 127°-128° C.; 1H NMR (CDCl3) δ: 2.75-3.0 (m, 3H), 3.3-3.5 (m, 2H), 3.8 (s, 3H), 3.95 (s, 3H), 693 (d, 1H), 7.25-7.4 (m, 5H), 7.9 (d, 1H).

Workup

temperatureheated at 100° C. for 0.25 h
additionwas added to the reaction mixture
customThe precipitate which formed
filtrationwas filtered
washwashed with 3×75 mL of water
dissolutiondissolved in 300 mL of methylene chloride
dry with materialThe methylene chloride solution was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-c15444310c7749b6894e111ab9d0b890
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05621133

Linked notes

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