Water → HCID 23432421, compound

HRID 2078675Notes

Reaction equation

HRID 2078675 reaction equation
O[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[C:30]([O-:33])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:18]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:15]=[CH:16][C:2]([O:33][CH2:30][CH2:11][CH2:10][CH2:9][CH2:8][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:16][CH3:15])=[CH:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 691504,4'-Dihydroxybenzophenone

Product 1

HCID 23432421HCID 23432421, compoundYield 149.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4,4′-dihydroxybenzophenone (21.4 g, 100 mmol), 1-bromododecane (49.8 g, 200 mmol), K2CO3 (50 g) in 500 mL of DMF were heated with stirring at 120° C. for 60 hours. After the mixture was cooled to room temperature, 1 L of water was added. The solution was extracted with CH2Cl2 (4×500 mL). The combined organic layers were dried with MgSO4 and the most of the solvent removed under reduced pressure as a white solid formed. The solids were collected by filtration, washed with cold hexanes, and air dried to give 4,4′-didodecyloxybenzophenone (41.2 g, 75%). A mixture of 4,4′didodecyloxybenzophenone (20.6 g) and hydrazine monohydrate (20 mL) in 150 mL of pentanol were heated at reflux for 24 hours. After cooling to room temperature, a white solid precipitated which is collected by vacuum filtration, washed with 20 mL cold ethanol and air dried (19.4 g, 92%).

Workup

  1. temperaturewere heated
  2. temperatureAfter the mixture was cooled to room temperature
  3. extractionThe solution was extracted with CH2Cl2 (4×500 mL)
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. customthe most of the solvent removed under reduced pressure as a white solid
  6. customformed
  7. filtrationThe solids were collected by filtration
  8. washwashed with cold hexanes, and air
  9. customdried

Sources & evidence

ORD record
ord-b13884c481b847eb99882d093761461d
Source dataset
uspto-grants-2011_04
Patent number
US07928432B2

Reaction notes

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