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1-Bromo-4-ethylbenzene → α-(4-Ethylphenyl)-2-(phenylmethoxy)benzenemethanol

HRID 909809
Notes
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Reaction equation

HRID 909809 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=1.[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>BrC1C=CC(CC)=CC=1.O1CCCC1>[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=1)[OH:22])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 153131-Bromo-4-ethylbenzeneHCID 25517Ammonium ChlorideHCID 3447842-(Benzyloxy)benzaldehydeHCID 5462224Magnesium

Product 1

HCID 67069123α-(4-Ethylphenyl)-2-(phenylmethoxy)benzenemethanolYield 101.4%

Reagents, catalysts & solvents 2

HCID 15313
1-Bromo-4-ethylbenzene
Catalyst
HCID 8028TetrahydrofuranSolvent3×

Procedure

1-Bromo-4-ethylbenzene (6.69 g, 0.036 mol) was added to a suspension of magnesium (17.2 g) and tetrahydrofuran (50 mL) and heated to reflux. Subsequently, a tetrahydrofuran (300 mL) solution of 1-bromo-4-ethylbenzene (97.9 g, 0.529 mol) was added for two hours at room temperature. After stirred at room temperature for 1.5 hours, the reaction mixture was cooled to 4° C. and a tetrahydrofuran (100 mL) solution of 2-benzyloxybenzaldehyde (100 g, 0.471 mol) was added for one hour. After stirred for two hours, the reaction mixture was poured into a saturated ammonium chloride aqueous solution. After the mixture was extracted with ethyl acetate, the organic phase was washed with brine and then dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=95:5) to obtain (2-benzyloxyphenyl)(4-ethylphenyl)methanol (152 g) as a colorless solid.

Workup

  1. temperatureheated to reflux
  2. temperaturethe reaction mixture was cooled to 4° C.
  3. stirringAfter stirred for two hours
  4. extractionAfter the mixture was extracted with ethyl acetate
  5. washthe organic phase was washed with brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationAfter the desiccant was filtered off
  8. customthe residue obtained
  9. customby evaporating the solvent under reduced pressure
  10. customwas purified by silica gel column chromatography (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-fc38e49fb1ca4d2a982933a1f1e478d4
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08017792B2

Reaction notes

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