2,4-Dichlorobenzaldehyde → HCID 68296064, compound
Reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[Cl:33][C:34]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:35]=1[CH:36]=O>>[Cl:33][C:34]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:35]=1[CH:36]=[CH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]Participants
Procedure
By the similar procedure of compound B7, B2 (2.25 g, 4.38 mmol) and 2,4-dichlorobenzaldehyde (500 mg, 2.86 mmol) were used as starting materials to afford (10 E or 10Z))-11-(2,4-dichlorophenyl)undec-10-enoic acid (B9) (576 mg, 1.75 mmol, 61%). Then this compound (210 mg, 0.638 mmol) was dissolved in ethyl acetate (10 mL) and Pd/BaSO4 (21 mg) was then added. The mixture was stirred at room temperature under hydrogen for 12 h. The mixture was filtered through Celite pad and washed with ethyl acetate. The combined filtrate was concentrated and dried in vacuum to afford compound B16 (210 mg, 0.634 mmol, 99%) as white solids. mp: 78° C. 1H-NMR (CDCl3, 400 MHz) δ 7.32 (d, J=1.9 Hz, 1H), 7.09-7.15 (m, 2H), 2.65 (t, J=7.8 Hz, 2H), 2.33 (t, J=7.5 Hz, 2H), 1.53-1.63 (m, 4H), 1.26 (m, 12H). 13C-NMR (CDCl3, 100 MHz) δ 180.00, 162.19, 159.80, 130.90, 125.31, 110.69, 103.44, 34.11, 30.15, 29.44, 29.36, 29.33, 29.19, 29.16, 29.03, 28.41, 24.69. HRMS (ESI) calculated for C17H24Cl2O2Na [M+Na]+: 353.1051, found: 353.1046.
Sources & evidence
- ORD record
- ord-d5b24de24b92471e86afd3dba1b66320
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181292B2
Reaction notes
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