Water → Methyl 2-(4-formylphenyl)acetate

HRID 339939Notes

Reaction equation

HRID 339939 reaction equation
C[N+]1([O-])CC[O:5]CC1.Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=1.O>CC#N.C1(C)C=CC=CC=1>[CH:10]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=1)=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetate

Product 1

HCID 19363032Methyl 2-(4-formylphenyl)acetate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a mixture of N-methylmorpholine-N-oxide (63.9 g, 545 mmol) in MeCN (848 g) and toluene (742 g), was added a solution of methyl [4-(bromomethyl)phenyl]acetate (53.0 g) in toluene (212 g) at 0 to 25° C. After stirring for 5 hr, water (106 g) was added to the reaction mixture. The aqueous layer was removed and remaining MeCN in the organic layer was removed under reduced pressure. The remaining toluene solution was washed with water twice (530 g×2), and concentrated under reduced pressure at a temperature below 40° C. until the weight of the solution was 233 g. An activated charcoal (3 g) was added to the solution and removed by filtration. To the solution was added 2,6-dibutyl-4-hydroxytoluene (152 mg), and concentrated under reduced pressure to give the subtitle compound. Yield 30.9 g, 79% from methyl [4-(bromomethyl)phenyl]acetate; 1H NMR (DMSO-d6) δ 9.99 (s, 1H), 7.87 (d, 2H), 7.86 (d, 2H), 3.83 (s, 2H), 3.63 (s, 3H)

Workup

  1. customThe aqueous layer was removed
  2. customwas removed under reduced pressure
  3. washThe remaining toluene solution was washed with water twice (530 g×2)
  4. concentrationconcentrated under reduced pressure at a temperature below 40° C. until the weight of the solution
  5. additionAn activated charcoal (3 g) was added to the solution
  6. customremoved by filtration
  7. additionTo the solution was added 2,6-dibutyl-4-hydroxytoluene (152 mg)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03484f212d3d478bbb1253f055dc89be
Source dataset
uspto-grants-2014_11
Patent number
US08895570B2

Reaction notes

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