4-METHOXYBENZOIN → HCID 131717098, compound

HRID 1460899Notes

Reaction equation

HRID 1460899 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[OH:12])=[O:10])=[CH:5][CH:4]=1.[C:19]1(=[O:25])[O:24][C:22](=[O:23])[CH2:21][CH2:20]1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[C:19]([OH:24])(=[O:25])[CH2:20][CH2:21][C:22]([OH:2])=[O:23].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[OH:12])=[O:10])=[CH:7][CH:8]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[OH:12])=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 37914-METHOXYBENZOINHCID 7922Succinic anhydrideHCID 516892Sodium Bicarbonate

Product 1

HCID 131717098HCID 131717098, compoundYield 125.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4-methoxybenzoin (20 g, 0.083 mole) and succinic anhydride (9.1 g, 0.091 mole) in toluene (6 mL) is heated for 7 hours under nitrogen at 135° C. (internal temp.). The solution is poured into 0.5N-NaHCO3, the organic layer was separated and reextracted with 0.5N-NaHCO3. The combined extracts are washed with ether and then acidified in the cold with concentrated HCl. The liberated oil is extracted with ethyl acetate (3×), the extracts washed with water and dried (MgSO4). Removal of the solvent yields a yellow solid (20.89 g, 73.8%), m.p. 104°-108° C. It is used in the next step without further purification.

Workup

  1. customthe organic layer was separated
  2. washThe combined extracts are washed with ether
  3. extractionThe liberated oil is extracted with ethyl acetate (3×)
  4. washthe extracts washed with water
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-d9eb4485807240f8b9d2bf3c84b0fac2
Source dataset
uspto-grants-1991_12
Patent number
US05071988

Reaction notes

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