Methylhydroquinone → 4-Benzoyloxy-2-methylphenol

HRID 277649

Reaction equation

HRID 277649 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]=1

Participants

3

Reactant 2

HCID 7253MethylhydroquinoneHCID 7412Benzoyl chloride

Product 1

HCID 146503304-Benzoyloxy-2-methylphenolYield 68.2%

Procedure

Using 2.5 g of methylhydroquinone and 2.8 g of benzoyl chloride, the procedure in Reference Example was followed. Recrystallization from ethanol-isopropyl ether gave 3.1 g of 4-benzoyloxy-2-methylphenol as white crystals, m.p. 120-122° C. Then, using 2.3 g of the 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 3 and 4 were followed to give 3.2 g of white crystals, m.p. 192-194° C. (decomp.).

Workup

  1. customRecrystallization from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-1e798493ce78462eb830a138848a9708
Source dataset
uspto-grants-2002_03
Patent number
US06358515B2

Linked notes

Loading…