Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16].Cl>O.C(Cl)Cl>[OH:9][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16]Participants
7
Procedure
To a 1,000-mL, three-neck, nitrogen-purged flask was added 26.5 g (0.21 mole) of 3-methoxyphenol, 215 mL of methylene chloride, 32 g (0.24 mole) of aluminum chloride and 32 mL (0.26 mole) of phenyl chloroformate. This mixture was heated to reflux. After 24 hours, the mixture was cooled to 20°-30° C. and 400 mL of water and 32 mL of 37% hydrochloric acid were added. The layers were separated and the organic layer washed with two 100-mL portions of 5N hydrochloric acid. The organic layer was dried with anhydrous magnesium sulfate, filtered, then the solvent stripped off under vacuum. The crude product was recrystallized from heptane. The yield of phenyl 2-hydroxy-4-methoxybenzoate (white, m.p. 61.5°-62.5° C.) obtained was 49%.
Workup
- customTo a 1,000-mL, three-neck, nitrogen-purged flask
- temperatureThis mixture was heated to reflux
- temperaturethe mixture was cooled to 20°-30° C.
- customThe layers were separated
- washthe organic layer washed with two 100-mL portions of 5N hydrochloric acid
- dry with materialThe organic layer was dried with anhydrous magnesium sulfate
- filtrationfiltered
- customThe crude product was recrystallized from heptane
Sources & evidence
- ORD record
- ord-d1d2494460a54e949443536b26301acf
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04454340
Linked notes
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