p-Toluenesulfonic acid → HCID 86759440, compound
Reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:26]([OH:32])[CH2:27][O:28][CH2:29][CH2:30]O>>[C:1]1([CH2:11][C:12]([O:14][CH2:30][CH2:29][O:28][CH2:27][CH2:26][OH:32])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 1-naphthylacetic acid (5) (2.0 g, 0.011 mol), PTSA (200 mg, 1.1 mmol), and diethylene glycol (6) (8 ml, 72.8 mmol) was stirred at 120° C. under N2. The reaction mixture became homogeneous after 1 h, and the stirring was continued for 15 h. After the reaction was completed (confirmed by TLC), the reaction mixture was poured into 50 ml of icewater mixture. The aqueous reaction mixture was extracted by EtOAc (3×50 ml) and dried over anhydrous MgSO4. The crude product was purified by column chromatography (SiO2, EtOAc/hexanes: 8/2) to yield 2.25 g (76%) of 7 as a colorless oil. 1H NMR (CDCl3, 500 MHz, 20° C.): d 7.83 (d, 1H, J=7.1 Hz ), 7.72-7.64 (m, 2H), 7.40-7.26 (m, 4H), 4.11 (t, 2H, J=4.7Hz), 3.96 (s, 2H), 3.46 (overlapped m, 4H), 3.26 (t, 2H, J=4.4 Hz), 1.90 (s, 1H). 13C NMR (CDCl3, 90 MHz, 20° C.): d 171.7, 134.0, 132.2, 130.6, 128.9, 128.2, 126.5, 126.0, 125.7, 123.9, 72.4, 65.8, 64.2, 61.2, 39.3.
Workup
- waitthe stirring was continued for 15 h
- additionthe reaction mixture was poured into 50 ml of icewater mixture
- extractionThe aqueous reaction mixture was extracted by EtOAc (3×50 ml)
- dry with materialdried over anhydrous MgSO4
- customThe crude product was purified by column chromatography (SiO2, EtOAc/hexanes: 8/2)
Sources & evidence
- ORD record
- ord-e4dbcb93201a4ed8b8c2a0a57e15f56c
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06733883B2
Reaction notes
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