m-Chloroperbenzoic acid → 2-(Benzyloxy)-3-(tert-butyl)benzaldehyde

HRID 1042515Notes

Reaction equation

HRID 1042515 reaction equation
[C:1]([C:5]1[C:6]([OH:13])=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].Cl[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21](OO)=O)[CH:16]=1>ClCCl>[CH2:21]([O:13][C:6]1[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 36786753-tert-Butyl-2-hydroxybenzaldehyde

Product 1

HCID 115435672-(Benzyloxy)-3-(tert-butyl)benzaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-tert-butyl-2-hydroxybenzaldehyde (20 g, 74.53 mmol) in dichloromethane (400 mL) was treated with m-chloroperbenzoic acid (70%, 20 g) in 3 portions at room temperature. Stirring was continued overnight. The reaction mixture was diluted with dichloromethane (to 1 L) and washed with saturated sodium bicarbonate (2×400 mL) and water (500 mL). The organic layer was dried over sodium sulfate and filtered. The solvent was removed in a rotary evaporator. The residue was taken up in methanol (375 mL), potassium hydroxide (7.5 g) was added and this mixture was stirred at room temperature overnight. The solvent was removed in a rotary evaporator. The residue was taken up in water (250 mL) and made acidic with 6N hydrochloric acid. The aqueous phase was extracted with ethyl acetate (800 mL). The organic extract was washed with water (300 mL), dried over sodium sulfate and the solvent was removed in a rotary evaporator. The crude product was purified by chromatography on silica (350 g) with 5% ethyl acetate in heptane (4 L). Pure 9 (16 g, 83%) was isolated.

Workup

  1. washwashed with saturated sodium bicarbonate (2×400 mL) and water (500 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed in a rotary evaporator
  5. additionpotassium hydroxide (7.5 g) was added
  6. stirringthis mixture was stirred at room temperature overnight
  7. customThe solvent was removed in a rotary evaporator
  8. extractionThe aqueous phase was extracted with ethyl acetate (800 mL)
  9. extractionThe organic extract
  10. washwas washed with water (300 mL)
  11. dry with materialdried over sodium sulfate
  12. customthe solvent was removed in a rotary evaporator
  13. customThe crude product was purified by chromatography on silica (350 g) with 5% ethyl acetate in heptane (4 L)

Sources & evidence

ORD record
ord-9344490ad32e45f99addcef255bb1548
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Reaction notes

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