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

HRID 1356491Notes

Reaction equation

HRID 1356491 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+].O>C(O)(CC)C>[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

6

Reactant 4

HCID 962WaterHCID 89191-BromododecaneHCID 516892Sodium BicarbonateHCID 519532(4-Chlorophenyl)(2,4-dihydroxyphenyl)methanone

Product 1

HCID 120842972-Hydroxy-4-dodecyloxy-4'-chlorobenzophenone

Reagents, catalysts & solvents 1

HCID 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 is heated in 77.6 g of sec-butanol and 25.6 g of water and refluxed for 20 hours. The reaction mixture is then stirred for 15 minutes in the presence of 0.8 g of active carbon and filtered while warm. The product crystallizes upon cooling. After recrystallization from sec-butanol, 21.5 g of pale yellow crystals are obtained having a melting point of 61-63° C.

Workup

  1. filtrationfiltered
  2. temperaturewhile warm
  3. customThe product crystallizes
  4. temperatureupon cooling
  5. customAfter recrystallization from sec-butanol, 21.5 g of pale yellow crystals
  6. customare obtained

Sources & evidence

ORD record
ord-438c9b900c2f440488ed94b3ae9f335a
Source dataset
uspto-grants-2003_07
Patent number
US06586519B1

Reaction notes

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