Dimethyl 4,4'-(3-oxopenta-1,4-diene-1,5-diyl)dibenzoate → HCID 21256018, compound

HRID 1647904Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13](=[O:26])[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=2)=[CH:7][CH:6]=1)=[O:4]>[Pd].CC(O)C>[CH3:25][O:24][C:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][C:13](=[O:26])[CH2:12][CH2:11][C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[CH:21][CH:20]=1)=[O:23]

Participants

Conditions

Temperature: 50 °C

Procedure

A heterogeneous mixture of 71.7 g of 1,5-bis-(4'-methoxycarbonyl-phenyl)-1,4-pentadien-3-one, 3.8 grams of 5% Pd on carbon, and 650 mL of 2-propanol was prepared in a 1 L 3-necked flask. The mixture was stirred mechanically and heated to 50° C. The system was flushed with hydrogen, and hydrogen was then supplied on a continuous basis at about 20 psi. The hydrogen uptake was initially very rapid, but gradually slowed. When hydrogen uptake nearly ceased, the hydrogen source was removed. The vessel was heated to 75°-80° C. and purged thoroughly with nitrogen. The hot product was filtered through a steam-jacketed Buchner funnel which contained a pad of filter-aid. The hot filtrate immediately began to precipitate the product.

Workup

customwas prepared in a 1 L 3-necked flask
customThe system was flushed with hydrogen, and hydrogen
customthe hydrogen source was removed
temperatureThe vessel was heated to 75°-80° C.
custompurged thoroughly with nitrogen
filtrationThe hot product was filtered through a steam-jacketed Buchner funnel which
filtrationof filter-aid
customto precipitate the product

Sources & evidence

ORD record: ord-461bb80106e64c00843cab7d07d98b91
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05434236

Reaction notes

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