Ethylene → 2-Vinyl-6-methoxynaphthalene
Reaction equation
BrC1C=C2C(=CC=1)C=C(O)C=C2.[CH3:13][C@H:14](C(O)=O)[C:15]1[CH:16]=[CH:17][C:18]2[CH:19]=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=2[CH:24]=1.BrC1C=C2C(=CC=1)C=C(OC)C=C2.C=C>>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][C:23]2[C:18](=[CH:17][CH:16]=[C:15]([CH:14]=[CH2:13])[CH:24]=2)[CH:19]=1Participants
5
Procedure
When it is desired to convert the 6-bromo-2-naphthol to naproxen, the 6-bromo-2-naphthol is first converted to a 6-bromo-2-methoxynaphthalene intermediate as described above, and the intermediate is then converted to naproxen by any of the techniques already known for that conversion. For example, as disclosed in U.S. Pat. No. 5,536,870 (Wu), the 6-bromo-2-methoxynaphthalene may be reacted with ethylene to form 2-methoxy-6-vinylnapthalene, which is then carbonylated to racemic 2-(6-methoxy-2-naphthyl)propionic acid, which can be subsequently resolved to isolate the desired naproxen enantiomer.
Sources & evidence
- ORD record
- ord-574962bf6f8e4d5eb4b6b6abd0bbe25f
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06121500
Reaction notes
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