Sodium Hydroxide → 3-[4-(Benzyloxy)-3-methoxyphenyl]-2,2-dimethylpropanal

HRID 1860673Notes

Reaction equation

HRID 1860673 reaction equation
[OH-:1].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]Cl)=[CH:13][C:12]=1[O:19][CH3:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.O>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:4]([CH3:9])([CH3:5])[CH:3]=[O:1])=[CH:13][C:12]=1[O:19][CH3:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 2979621-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzene

Product 1

HCID 186241843-[4-(Benzyloxy)-3-methoxyphenyl]-2,2-dimethylpropanal

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 241BenzeneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Under argon, a mixture of sodium hydroxide (1.43 g, 35.85 mmol) and tetrabutylammonium iodide (0.30 g, 0.82 mmol) in 8 ml benzene and 2.8 ml H2O was heated at 70° C. to form a homogeneous mixture. A mixture of the product of Step 1 (8.05 g, 30.64 mmol) and isobutraaldehyde (2.95 g, 40.85 mmol) in 20 ml benzene was added to the above solution dropwise. The resulting reaction mixture was heated at 70-75° C. for 6 h. The product was extracted with ethyl acetate and washed with H2O. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried with MgSO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/9) to yield a colorless oil in 8.32 g. NMR spectra of the product were consistent for the proposed structure.

Workup

  1. customto form a homogeneous mixture
  2. additionwas added to the above solution dropwise
  3. customThe resulting reaction mixture
  4. temperaturewas heated at 70-75° C. for 6 h
  5. extractionThe product was extracted with ethyl acetate
  6. washwashed with H2O
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic layer was washed with brine
  9. dry with materialdried with MgSO4
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/9)
  12. customto yield a colorless oil in 8.32 g

Sources & evidence

ORD record
ord-1e490710f6cc49a1bc9e06fbd5f6b380
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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