O-Cresol → HCID 12414461, compound

HRID 1111272Notes

Reaction equation

HRID 1111272 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]O.[C:10]1([CH3:17])[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][CH:11]=1.C([Mg]Br)C>CCOCC>[CH3:17][C:10]1[C:15]([OH:16])=[C:14]([CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[OH:1])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 335O-CresolHCID 5146Salicyl AlcoholHCID 178418443HCID 178418443, compound

Product 1

HCID 12414461HCID 12414461, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Hydroxybenzyl alcohol (18.6 g, 0.15 mol) and o-cresol (16.2 g, 0.15 mol) were dissolved in 150 ml of ether in a flask and a dry nitrogen atmosphere established. Ethyl magnesium bromide (100 ml of 3M solution in ether, 0.30 mol) was added dropwise with stirring. The ether was removed by evaporation under reduced pressure and 450 ml of benzene added. The resulting mixture was heated at reflux with stirring for 20 hours and then allowed to cool. Saturated aqueous ammonium chloride solution was added and the mixture extracted with 2-500 ml portions of ether. The combined ether extracts were dried over magnesium sulfate and the ether then removed by evaporation. The residue was chromatographed on a silica gel column eluting with an 80:20 mixture of hexane and ethyl acetate and dried in a vacuum oven at 100° C. to obtain 7.6 g (24 percent of theory) of (3-methyl-2-hydroxyphenyl) (2-hydroxyphenyl)methane as an oil.

Workup

  1. customThe ether was removed by evaporation under reduced pressure and 450 ml of benzene
  2. additionadded
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux
  5. stirringwith stirring for 20 hours
  6. temperatureto cool
  7. additionSaturated aqueous ammonium chloride solution was added
  8. extractionthe mixture extracted with 2-500 ml portions of ether
  9. dry with materialThe combined ether extracts were dried over magnesium sulfate
  10. customthe ether then removed by evaporation
  11. customThe residue was chromatographed on a silica gel column
  12. washeluting with an 80:20 mixture of hexane and ethyl acetate
  13. customdried in a vacuum oven at 100° C.

Sources & evidence

ORD record
ord-53f757bbf0584f4aaf42afc04d86da7f
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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