m-Chloroperbenzoic acid → HCID 86657502, compound

HRID 56531Notes

Reaction equation

HRID 56531 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[CH3:11])C=O.ClC1C=C(C=CC=1)[C:18]([O:20]O)=[O:19]>C(Cl)Cl>[CH:18]([O:20][C:5]1[CH:8]=[C:9]([O:12][CH3:13])[C:10]([CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 110952183,5-Dimethoxy-4-methylbenzaldehyde

Product 1

HCID 86657502HCID 86657502, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,5-dimethoxy-4-methylbenzaldehyde (3.0 g, 16.8 mmol) in CH2Cl2 (35 mL) was added meta-chloroperoxybenzoic acid (77% purity; 5.8 g, 25.9 mmol). After stirring at room temperature for 19 hrs, additional meta-chloroperoxybenzoic acid (77% purity; 3.5 g, 15.6 mmol) was added. After heating for 4 hrs at 40° C. and cooling to room temperature, 10% aqueous Na2S2O5 was added and the mixture was stirred for 30 min. The mixture was diluted with CH2Cl2 and the layers separated. The organics were washed with 10% aqueous Na2S2O5, ˜5% aqueous NaHCO3 and brine then dried over MgSO4 and concentrated to give 3,5-dimethoxy-4-methylphenyl formate as a yellow solid (2.9 g, 88% yield).

Workup

  1. temperatureAfter heating for 4 hrs at 40° C.
  2. temperaturecooling to room temperature
  3. stirringthe mixture was stirred for 30 min
  4. customthe layers separated
  5. washThe organics were washed with 10% aqueous Na2S2O5, ˜5% aqueous NaHCO3 and brine
  6. dry with materialthen dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8ac28ef8853a4a89b6dd9cd30641d29e
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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