Reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.S(OC)(O[CH3:21])(=O)=O>O>[CH3:21][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
120 ml of water and sodium hydroxide (14.00 g, 0.35 mol) were placed in a conical flask and dissolved. 4,4'-Dihydroxybiphenyl (28.00 g, 0.15 mol) was then added and heated to reflux for 2 hours with stirring using a condenser. Dimethyl sulfate (14.5 ml, 0.15 mol) was added dropwise over about 40 minutes. After addition, the mixture was heated while stirring for 2 hours, and then allowed to cool and filtrated. The filter cake was transferred into 700 ml of water, which was then heated to boiling temperature, and filtrated while still keeping warm. The filtrate was kept at 70° C., and 20% hydrochloric acid was added. White precipitation: formed was washed extensively. Recrystallization from ethanol yielded 4'-methoxy-4-hydroxybiphenyl (13.17 g, Yield: 48.0%).
Workup
- dissolutiondissolved
- temperatureheated
- temperatureto reflux for 2 hours
- additionAfter addition
- temperaturethe mixture was heated
- stirringwhile stirring for 2 hours
- temperatureto cool
- filtrationfiltrated
- temperaturewas then heated
- filtrationfiltrated
- temperaturewhile still keeping warm
- customwas kept at 70° C.
- addition20% hydrochloric acid was added
- customWhite precipitation
- customformed
- washwas washed extensively
- customRecrystallization from ethanol
Sources & evidence
- ORD record
- ord-22bc116db45d424b96b7e0d2b5e88843
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05412079
Linked notes
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