Hexane → HCID 46205463, compound

HRID 909769Notes

Reaction equation

HRID 909769 reaction equation
CCCCCC.Br[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=1.[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=[O:22].[Cl-].[NH4+]>O1CCCC1>[Br:17][C:18]1[CH:19]=[C:20]([CH:21]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[OH:22])[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 685234-BromophenetoleHCID 765833-Bromobenzaldehyde

Product 1

HCID 46205463HCID 46205463, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2.6 M n-butylithium hexane solution (5.8 mL) was added to a mixture of 4-bromophenetole (2.87 g, 0.0143 mol) and tetrahydrofuran (30 mL) at −78° C. After the mixture was stirred for 0.5 hours, a tetrahydrofuran (15 mL) solution of 3-bromobenzaldehyde (2.65 g, 0.0143 mol) was added, and further stirred for 15 minutes to warm the reaction mixture to room temperature. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic layer was washed with brine and 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=7:1 to 5:1) to obtain colorless oily (3-bromophenyl)(4-ethoxyphenyl)methanol (3.94 g, 90%).

Workup

  1. stirringfurther stirred for 15 minutes
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. customthe residue obtained
  7. customby evaporating the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=7:1 to 5:1)

Sources & evidence

ORD record
ord-73980847e4764a778e1ed6d0cea4dae8
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

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