Cuminaldehyde → (2-Benzyloxyphenyl)-(4-isopropylphenyl)methanol

HRID 554498Notes

Reaction equation

HRID 554498 reaction equation
CCCCCC.C([Li])CCC.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:27]([C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1)([CH3:29])[CH3:28].O>C1COCC1>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:34]([C:33]1[CH:36]=[CH:37][C:30]([CH:27]([CH3:29])[CH3:28])=[CH:31][CH:32]=1)[OH:35])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 326CuminaldehydeHCID 962WaterHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 67459620(2-Benzyloxyphenyl)-(4-isopropylphenyl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (2.44 M, 5.14 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (3.0 g, 11.4 mmol) in THF (114 mL) at −78° C. and the reaction mixture was stirred at the same temperature for 30 minutes. To this solution, a solution of 4-isopropylbenzaldehyde (1.41 g, 9.49 mmol) in THF (38 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for one hour and furthermore at 0° C. for one hour. Water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (2.63 g, 84%).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for one hour and furthermore at 0° C. for one hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

Sources & evidence

ORD record
ord-f2976ad2a9a04cc49d3278293327f678
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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