Acetic Acid → HCID 13621301, compound

HRID 464744Notes

Reaction equation

HRID 464744 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15](Br)Br)[C:10]=1[CH2:18]Br)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O-:23])(=[O:22])[CH3:21].[Na+].C(O)(=[O:27])C>O>[C:20]([O:23][CH2:18][C:10]1[C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=[CH:12][C:11]=1[CH:15]=[O:27])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 13621300HCID 13621300, compound

Product 1

HCID 13621301HCID 13621301, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of crude 1-benzoyl-2-bromomethyl-3-(dibromomethyl)benzene (2.3 g, 5 mmol) in glacial acetic acid (30 ml) was added sodium acetate (4.5 g, 55 mmol) in water (8 ml). The stirred mixture was heated to reflux temperature for sixteen hours, cooled and partitioned between diethylether (100 ml), ethyl acetate (20 ml) and 10% sodium carbonate solution (100 ml). Further solid sodium carbonate was added until effervescence ceased. The organic layer was washed with 10% sodium carbonate solution (30 ml) and brine (30 ml) and dried over sodium sulphate. Removal of the solvent under reduced pressure gave an oil (1.1 g) that was chromatographed (SiO2 (40 g) using (4:1) pentane:ethyl acetate as eluent). This gave 2-acetoxymethyl-3-benzoylbenzaldehyde (0.35 g, 22% from 1-benzoyl-2,3-dimethylbenzene).

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureto reflux temperature for sixteen hours
  3. temperaturecooled
  4. custompartitioned between diethylether (100 ml), ethyl acetate (20 ml) and 10% sodium carbonate solution (100 ml)
  5. additionFurther solid sodium carbonate was added until effervescence
  6. washThe organic layer was washed with 10% sodium carbonate solution (30 ml) and brine (30 ml)
  7. dry with materialdried over sodium sulphate
  8. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-9c19fa71e52141c6a3814f5fbdec4ab0
Source dataset
uspto-grants-1985_10
Patent number
US04548948

Reaction notes

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