2-Hydroxy-5-methylacetophenone → HCID 18950993, compound

HRID 1492755Notes

Reaction equation

HRID 1492755 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=O)[CH3:10].C[O-].[Na+].Br[CH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[C:19]#[N:20]>CN(C=O)C.C(O)C.ClCCl.CO>[CH3:10][C:9]1[C:3]2[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[O:1][C:16]=1[C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[C:19]#[N:20]

Participants

8

Reactant 3

HCID 150682-Hydroxy-5-methylacetophenoneHCID 895992-(Bromomethyl)benzonitrileHCID 10942334Sodium Methoxide2×

Product 1

HCID 18950993HCID 18950993, compoundYield 32.3%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 1-(2-hydroxy-5-methylphenyl)ethanone (1 g) in DMF (7 ml) was added to a solution of sodium methoxide (0.39 g) in ethanol (7 ml). After about 10 min a solution of 2-(bromomethyl)benzonitrile (1.3 g) in DMF (7 ml) was added and the solution heated to 110° C. After 2 h further sodium methoxide (0.39 g) was added and heating at 110° C. continued. After a further 30 min, the reaction was cooled to room temperature and the ethanol evaporated. The solution was poured into water/ice (200 ml) and extracted into ethyl acetate (4×30 ml). The combined organic extracts were washed with water (4×20 ml) and dried. Filtration and evaporation gave a yellow oil which was then dissolved in dichloromethane (2 ml) and methanol (30 ml). Concentration gave a solid which was collected and washed with further methanol to give the title compound as a white solid (0.53 g).

Workup

  1. temperatureheating at 110° C.
  2. temperaturethe reaction was cooled to room temperature
  3. customthe ethanol evaporated
  4. additionThe solution was poured into water/ice (200 ml)
  5. extractionextracted into ethyl acetate (4×30 ml)
  6. washThe combined organic extracts were washed with water (4×20 ml)
  7. customdried
  8. filtrationFiltration and evaporation
  9. customgave a yellow oil which
  10. concentrationConcentration
  11. customgave a solid which
  12. customwas collected
  13. washwashed with further methanol

Sources & evidence

ORD record
ord-f7054e9770a648e69a239af5dbb76bd4
Source dataset
uspto-grants-1994_12
Patent number
US05374646

Reaction notes

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