Water → HCID 68487510, compound
Reaction equation
[CH3:1][C:2]1[C:3]([Cl:26])=[CH:4][C:5](C(C)(C)C)=[C:6]([C:9]2[C:10]([OH:21])=[C:11]([CH3:20])[C:12]([Cl:19])=[CH:13][C:14]=2C(C)(C)C)[C:7]=1[OH:8].C1(C)C=CC=CC=1.FC(F)(F)S(O)(=O)=O.O>C(Cl)(Cl)Cl>[CH3:20][C:11]1[C:12]([Cl:19])=[CH:13][CH:14]=[C:9]([C:6]2[C:7]([OH:8])=[C:2]([CH3:1])[C:3]([Cl:26])=[CH:4][CH:5]=2)[C:10]=1[OH:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
The optically active 6,6′-dimethyl-5,5′-dichloro-3,3′-di(t-butyl)-2,2′-biphenol obtained in Example 6 (110 mg, optical purity: >99% ee, 0.28 mmol), toluene (5 ml) and trifluoromethanesulfonic acid (45 mg, 0.5 mmol) were mixed followed by stirring the entire volume for 1 hour at 5° C. Water (1 ml) and chloroform were then added to the reaction mixture followed by extraction and liquid separation. The organic phase was then washed with water and dried with anhydrous magnesium sulfate followed by distilling off the solvent under reduced pressure. N-hexane (10 ml) was added to the remaining slurry followed by stirring at room temperature, washing and filtering to obtain optically active 6,6′-dimethyl-5,5′-dichloro-2,2′-biphenol (70 mg, yield: 82%, optical purity: >99% ee).
Workup
- extractionfollowed by extraction and liquid separation
- washThe organic phase was then washed with water
- dry with materialdried with anhydrous magnesium sulfate
- distillationby distilling off the solvent under reduced pressure
- additionN-hexane (10 ml) was added to the remaining slurry
- stirringby stirring at room temperature
- washwashing
- filtrationfiltering
Sources & evidence
- ORD record
- ord-baab4d94b18c4d43b0a294f35cd23df9
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283501B2
Reaction notes
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