Reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:3]=1[OH:4].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:10]([O:9][C:7]1[CH:6]=[CH:5][C:3]([OH:4])=[C:2]([CH3:1])[CH:8]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Procedure
Using 5.0 g of methylhydroquinone and 5.6 g of benzoyl chloride, the procedure of Reference Example was followed. Recrystallization from ethanol-isopropyl ether gave 6.2 g of 4-benzoyloxy-2-methylphenol as white crystals, m.p. 120-122. Then, using 6.2 g of thus obtained white crystals, 5.1 g of benzyl bromide and 4.1 g of anhydrous potassium carbonate, the procedure of Reference Example was followed to give 7.6 g of 1-benzyloxy-2-methyl-4-benzoyloxybenzene as white crystals, m.p. 118-119° C. Then, using 7.6 g of thus obtained white crystals, 15 ml of 2N NaOH and 100 ml of methanol, the procedure of Reference Example was followed to give 3.8 g of 4-benzyloxy-3-methylphenol as white crystals, m.p. 70-71° C. Then, using 2.1 g of thus obtained white crystals, 1.4 g of anhydrous potassium carbonate, 4.6 g of chloromethyloxirane and 1.9 g of 1-(2-methoxyphenyl)piperazine, the procedures of Examples 1-A and 2 were followed. Recrystallization from methanol-ethyl acetate gave 3.0 g of white crystals, m.p. 214-216° C. (decomp.).
Workup
- customRecrystallization from ethanol-isopropyl ether
Sources & evidence
- ORD record
- ord-6b00fa4521564013894a818b385466b3
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06358515B2
Linked notes
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