Ethanol → HCID 21469848, compound

HRID 2295135Notes

Reaction equation

HRID 2295135 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C([O-])C.[Na+].C(O)C.Br[CH2:24][CH2:25][CH2:26][CH2:27][Cl:28]>C(OCC)(=O)C.CO>[Cl:28][CH2:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 143474-HydroxybenzophenoneHCID 813641-Bromo-4-chlorobutaneHCID 2723922Sodium ethoxide

Product 1

HCID 21469848HCID 21469848, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Combine 4-hydroxybenzophenone (347 g, 1.75 mol) and methanol (3.5 L). Heat to 50° C. and add a solution of sodium ethanolate in ethanol (718 mL, 21% by weight, 1.92 mol) over 20 minutes. Heat to reflux and add 1-bromo-4-chlorobutane (600 g, 3.5 mol) over 30 minutes. After 18 hours, cool the reaction mixture and evaporate in vacuo to obtain a residue. Add ethyl acetate (5 L) to give a solid. Filter and extract the filtrate with aqueous 10% sodium hydroxide solution and aqueous saturated sodium chloride solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give 4-(4-chlorobutoxy)benzophenone.

Workup

  1. temperatureHeat
  2. temperatureto reflux
  3. temperaturecool the reaction mixture
  4. customevaporate in vacuo
  5. customto obtain a residue
  6. filtrationFilter
  7. extractionextract the filtrate with aqueous 10% sodium hydroxide solution and aqueous saturated sodium chloride solution
  8. dry with materialDry the organic layer over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo

Sources & evidence

ORD record
ord-2c4ec2fd2e3544a589a1bdca82c7a964
Source dataset
uspto-grants-1997_11
Patent number
US05691384

Reaction notes

Loading…