Methanol → (1,1'-Biphenyl)-2,3'-diol

HRID 1608885Notes

Reaction equation

HRID 1608885 reaction equation
[CH:1]1([C:7](OC)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([Mg]Br)=[CH:15][CH:14]=1.[OH:21]S(O)(=O)=O.I[Si](C)(C)C.[CH2:31](S)[CH2:32][CH2:33][CH3:34].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:40][CH2:41]S.[Al+3].[Cl-].[Cl-].[Cl-].CCS.C(S)CCC.[CH3:55][OH:56]>N1C=CC=CC=1.C(Cl)Cl.C(O)(=O)C>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:7]([C:1]2[CH:2]=[CH:3][C:4]([O:56][CH3:55])=[CH:5][CH:6]=2)=[C:31]2[CH2:41][CH2:40][CH2:34][CH2:33][CH2:32]2)=[CH:15][CH:14]=1.[CH:16]1[CH:17]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[C:5]([OH:21])[CH:6]=2)[C:13]([OH:12])=[CH:14][CH:15]=1

Participants

14

Reactant 9

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6343EthanethiolHCID 8012ButanethiolHCID 20748Methyl cyclohexanecarboxylateHCID 85247Trimethylsilyl iodideHCID 19417624HCID 19417624, compoundHCID 19825052HCID 19825052, compoundHCID 178491912HCID 178491912, compound

Product 2

HCID 33665(1,1'-Biphenyl)-2,3'-diolHCID 824581-(Cyclohexylidene(4-methoxyphenyl)methyl)-4-methoxybenzene

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Bis-(p-methoxyphenyl)-cyclohexylidene methane 28 (FIG. 3) was prepared from methyl cyclohexane carboxylate 26 and p-methoxyphenyl magnesium bromide (Miquel et al., 1963). Dehydration of 27 was accomplished with a mixture of H2SO4 and acetic acid. While 29 was demethylated with iodotrimethylsilane in pyridine, 30 was difficult to isolate, and the demethylation was repeated using n-BuSH/AlCl3. However, the best method found for demethylation involved the use of EtSH/AlCl3 in CH2Cl2. EtSH has a lower boiling point than n-BuSH and offers the advantage of being easier to remove from the reaction mixture. Diphenol 30 underwent a gradual color change, but was obtained pure from the acid hydrolysis of the di-acetate 31.

Workup

  1. customto isolate
  2. customto remove from the reaction mixture

Sources & evidence

ORD record
ord-0608268a524c4c249b300e832adc827a
Source dataset
uspto-grants-1995_03
Patent number
US05397802

Reaction notes

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