Methane → 2-Hydroxy-4-dodecyloxy-4'-chlorobenzophenone

HRID 1292583Notes

Reaction equation

HRID 1292583 reaction equation
[OH:1][C:2]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(=O)([O-])O.[Na+].C>C(O)(CC)C.O>[OH:1][C:2]1[CH:16]=[C:15]([O:17][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[CH:10][CH:11]=1)=[O:5]

Participants

7

Reactant 4

HCID 297MethaneHCID 89191-BromododecaneHCID 516892Sodium BicarbonateHCID 519532(4-Chlorophenyl)(2,4-dihydroxyphenyl)methanone

Product 1

HCID 120842972-Hydroxy-4-dodecyloxy-4'-chlorobenzophenoneYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6568(+-)-2-ButanolSolvent

Procedure

A mixture of 20 g (80 mmol) of 2,4-dihydroxy-4'-chlorobenzophenone, 21.9 g (88 mmol) of 1-bromododecane and 8.4 g (100 mmol) of sodium hydrogen carbonate in 77.6 g of sec-butyl alcohol and 25.6 g of H2O is heated with stirring and maintained at reflux for 20 h. The reaction mixture is stirred for an additional 15 min in the presence of 0.8 g of activated charcoal and is then filtered while hot. After the filtrate has cooled, the product crystallizes. It is recrystallized from sec-butyl alcohol to give 21.5 g of pale yellow crystals having a melting point of 61°-63° C.

Workup

  1. temperatureis heated
  2. temperaturemaintained
  3. temperatureat reflux for 20 h
  4. filtrationis then filtered while hot
  5. temperatureAfter the filtrate has cooled
  6. customthe product crystallizes
  7. customIt is recrystallized from sec-butyl alcohol

Sources & evidence

ORD record
ord-4077fbbd5ffc4912b3743a37ddcfc6bb
Source dataset
uspto-grants-1998_05
Patent number
US05756793

Reaction notes

Loading…