2,4-Hexadien-1-ol → 4,4'-Di-2,4-hexadienoxybenzophenone

HRID 363548Notes

Reaction equation

F[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11](F)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:19]([OH:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH3:24]>CN(C=O)C>[CH2:19]([O:25][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:7][CH2:6][CH:5]=[CH:4][CH:3]=[CH:2][CH3:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)[CH:20]=[CH:21][CH:22]=[CH:23][CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

4,4'-Difluorobenzophenone (34) (4.8 grams, 22 mmol) was dissolved in anhydrous DMF (1 liter). NaH (95%; 5.6 grams, 220 mmol) was added and the solution was cooled to 0° C. 2,4-Hexadienol (5.8 mL, 51 mmol) was slowly added to the solution and the reaction mixture was allowed to warm to room temperature with stirring under argon overnight. The reaction mixture was concentrated in vacuo, dissolved in dichloromethane, and washed with water. The organic phase was dried (MgSO4) and concentrated and purified by column chromatography (silica gel; hexane/CH2Cl2, 1/3) to afford 2.07 grams (25%) of compound 35 as a white solid. 1H H NMR (300 MHz, DMSO-d6) δ1.73 (d, J=6.6 Hz, 6H), 4.68 (d, J=6.0 Hz, 4H), 5.69-5.84 (m, 4H), 6.05-6.19 (m, 2H), 6.31-6.45 (m, 2H), 7.08 (d, J=9.0 Hz, 4H), 7.68 (d, J=10.2 Hz, 4H).

Workup

temperatureto warm to room temperature
concentrationThe reaction mixture was concentrated in vacuo
dissolutiondissolved in dichloromethane
washwashed with water
dry with materialThe organic phase was dried (MgSO4)
concentrationconcentrated
custompurified by column chromatography (silica gel; hexane/CH2Cl2, 1/3)

Sources & evidence

ORD record: ord-ad308aeb976141c2818013435a3597f8
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05874532

Reaction notes

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