Toluene → Cresyl saligenin

HRID 1840714Notes

Reaction equation

HRID 1840714 reaction equation
C1COCC1.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([Mg]Br)=[CH:9][CH:8]=1.CCOCC.[CH:20](=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23].C1(C)C=CC=CC=1>O>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([CH:20]([OH:28])[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[OH:23])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6998SalicylaldehydeHCID 8028TetrahydrofuranHCID 178467760HCID 178467760, compound

Product 1

HCID 2751544Cresyl saligeninYield 112.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 ml round bottom flask containing 100 mL of THF under Ar was added commercial 1 M p-methylphenyl magnesium bromide/Et2O (100 mL, 100 mmol). Subsequently, salicylaldehyde (4.9 g, 40.3 mmol) was added dropwise in four equal portions spaced over 2 hr. After 20 min, once HPLC analysis revealed the aldehyde to be consumed, the reaction was quenched by dropwise addition of 26 ml of sat'd NH4Cl/H2O to produce a white paste. To this suspension was added 200 mL of PhMe and sufficient H2O to permit stirring. The organic layer was decanted whereupon the white paste was triterated a second time with 1:1 THF/PhMe. After decanting, the combined organic layers were concentrated using a rotary evaporator to obtain 9.7 g of crude 4-methyl-2′-hydroxybenzhydrol.

Workup

  1. waitAfter 20 min
  2. customto be consumed
  3. customthe reaction was quenched by dropwise addition of 26 ml of sat'd NH4Cl/H2O
  4. customto produce a white paste
  5. customThe organic layer was decanted whereupon the white paste
  6. customAfter decanting
  7. concentrationthe combined organic layers were concentrated
  8. customa rotary evaporator

Sources & evidence

ORD record
ord-17029519877c42ce830085fc3b4e9bf8
Source dataset
uspto-grants-2004_01
Patent number
US06683056B2

Reaction notes

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