Sodium Hydroxide → HCID 18470427, compound

HRID 2228891Notes

Reaction equation

HRID 2228891 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:10].[OH-:18].[Na+]>C(O)C>[OH:18][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18470194HCID 18470194, compound

Product 1

HCID 18470427HCID 18470427, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 8-bromo-1-(4-chlorophenyl)octan-1-one (4.0 g) in ethanol (170 ml) was added 3% aqueous sodium hydroxide (70 ml). The mixture was heated at reflux for 3 h, cooled and evaporated to one third volume. Water (50 ml) and dichloromethane (100 ml) were added. The organic layer was separated and the aqueous layer was re-extracted with dichloromethane (2×50 ml). The combined extracts were washed with water (30 ml) and dried over magnesium sulphate. The solvent was removed under reduced pressure and the residue was crystallised from 40-60° C. petroleum ether to give 8-hydroxy-1-(4-chlorophenyl)octan-1-one (1.0 g). 1H-NMR (CDCl3) δ 1.25-1.9 (10H, m), 2.94 (2H, t), 3.64 (2H, t), 7.43 (2H, m) and 7.89 (2H, m). (EI) Found M+=254. C14H19ClO2 requires 254.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. temperaturecooled
  4. customevaporated to one third volume
  5. additionWater (50 ml) and dichloromethane (100 ml) were added
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was re-extracted with dichloromethane (2×50 ml)
  8. washThe combined extracts were washed with water (30 ml)
  9. dry with materialdried over magnesium sulphate
  10. customThe solvent was removed under reduced pressure
  11. customthe residue was crystallised from 40-60° C. petroleum ether

Sources & evidence

ORD record
ord-3a9a63eadbb441deb33a8a3194f9c827
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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