4-Hydroxybenzaldehyde → HCID 2964812, compound

HRID 892848Notes

Reaction equation

HRID 892848 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18]>CS(C)=O.[Cl-].[Na+].O>[C:19]1([CH:17]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH3:18])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11454(1-Bromoethyl)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 2964812HCID 2964812, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (528 mg, 4.32 mmol) in dimethylsulfoxide (8 mL) was added potassium t-butoxide (558 mg, 4.97 mmol) and the mixture was stirred for 20 mins. 1-Bromoethylbenzene was added dropwise and the reaction was stirred for 1 hour at room temperature It was then poured into brine (8 mL) and extracted with ethyl acetate (3×10 mL). The organics were combined; dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 15:85) to afford 930 mg (95%) of 4-(1-phenylethoxy)benzaldehyde as an oil.

Workup

  1. stirringthe reaction was stirred for 1 hour at room temperature It
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. customThe resulting residue was chromatographed (silica gel, ether:hexanes, 15:85)

Sources & evidence

ORD record
ord-b3c3b45f3cd34c64818d0226cf5b4b3e
Source dataset
uspto-grants-1992_06
Patent number
US05120752

Reaction notes

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