4-Hydroxybenzaldehyde → 4-(3,3,3-Triphenylpropoxy)benzaldehyde
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1([C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:17][CH2:18]O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([C:16]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1Participants
Procedure
By the method of example 12, 4-hydroxybenzaldehyde was condensed with 3,3,3-triphenylpropanol to provide 4-(3,3,3-triphenylpropoxy)benzaldehyde, a white solid, mp 127°-130° C. after recrystallization from hexane (58% yield). This material (4.0 g, 10.2 mmol) was suspended in ethanol (100 mL), and sodium borohydride (0.2 g, 5.0 mmol) was added. After 3 hr, aqueous 1N HCl was added dropwise until gas evolution ceased. Precipitated boric acid was removed by filtration, and the flitrate concentrated to a gummy residue. This was partitioned between water and ether, and the ether solution dried (MgSO4), filtered, and concentrated. The residue was kept under high vacuum overnight to remove solvent, leaving 4-(3,3,3-triphenylpropoxy)benzyl alchohol as an amorphous solid (3.9 g, 97%). This material (3.9 g, 9.9 mmol) was dissolved in benzene (80 mL), and thionyl chloride (1.0 mL, 14 mmol) was added, followed by five drops of DMF at 5-minute intervals. The mixture was heated briefly to reflux, cooled, and concentrated to an oil which solidified on standing. Trituration of the solid with cold methanol provided 4-(3,3,3-triphenylpropoxy)benzyl chloride as a white powder, mp 91°-95° C. (83%). 1H NMR (CDCl3) δ 7.19-7.35 (m, 17H), 6.66 (d, J=8.7 Hz, 2H), 4.51 (s, 2H), 3.72 (t, J=7.8 Hz, 2H), 3.12 (t, J=7.8 Hz, 2H).
Sources & evidence
- ORD record
- ord-6204a97214054fb28b479e500bb306dc
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05643950
Reaction notes
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