Water → HCID 63323525, compound

HRID 1402922Notes

Reaction equation

HRID 1402922 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=O.[CH2:11](Br)[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].O>C(O)C>[C:12]([C:11]1[O:1][C:2]2[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=2[CH:4]=1)(=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 69184Benzaldehyde, 2-hydroxy-5-methyl-

Product 1

HCID 63323525HCID 63323525, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-hydroxy-5-methylbenzaldehyde (1 g) and phenacyl bromide (1.06 g) in ethanol (10 ml) potassium carbonate (2.03 g) was added. The mixture was stirred at 80° C. for 1 h. Then the reaction mixture was poured into water (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4), and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel (hexane/ethyl acetate 12:1) to give 2-benzoyl-5-methylbenzofuran (1.1 g) as yellowish solid.

Workup

  1. extractionextracted with dichloromethane (3×20 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by flash chromatography on silica gel (hexane/ethyl acetate 12:1)

Sources & evidence

ORD record
ord-43e61dba23864b59bdec8d34eeba178f
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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