Water → HCID 69028833, compound

HRID 1867782Notes

Reaction equation

HRID 1867782 reaction equation
CN(C)[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:18])[C:10]2[CH:15]=[C:14]([CH3:16])C=[CH:12][C:11]=2[OH:17])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35].O.[CH3:37][N:38]([CH3:41])[CH:39]=O>>[CH3:37][N:38]([CH3:41])[C:39]1[C:14]([CH3:16])=[CH:15][C:10]([C:9]([C:6]2[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=2)=[O:18])=[C:11]([O:17][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])[CH:12]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 900121-Octanol, 8-chloro-HCID 69029682HCID 69029682, compound

Product 1

HCID 69028833HCID 69028833, compound

Conditions

Temperature
100 °C

Procedure

In a 50 ml three-necked round-bottomed flask, 1.51 g (5.9 mmol) of 4′-dimethylamino-2-hydroxy-5-methylbenzophenone are dissolved in 10.5 ml of dimethylformamide. 3.24 g (23.17 mmol) of potassium carbonate are then added at room temperature. A temperature rise to approx. 30° C. is observed and the yellow solution immediately becomes orange. The suspension is heated to 100° C. Then, 1.46 g (8.614 mmol) of 8-chloro-1-octanol are added dropwise within 10 minutes. The dark-orange suspension is stirred at 100° C. for 2 hours and then cooled to room temperature. To dissolve the salts, 25 ml of water are added and the brown solution is then extracted using dichloromethane. The organic phase is washed with sodium hydrogencarbonate (w=0.095 g/g) and then concentrated on a rotary evaporator. The resulting brown oil is fractionally filtered through 200 g of silica gel (Merck 0.04-063 mesh) with 1 l of hexane/ethyl acetate (1:1), followed by 1 l of ethyl acetate. The ethyl acetate fraction is then concentrated by evaporation on a rotary evaporator. 1.97 g of a yellow oil are obtained, which crystallizes after 2 days (81.4% of theory); m.p.: 56.9° C.

Workup

  1. customto approx. 30° C.
  2. temperaturecooled to room temperature
  3. additionare added
  4. extractionthe brown solution is then extracted
  5. washThe organic phase is washed with sodium hydrogencarbonate (w=0.095 g/g)
  6. concentrationconcentrated on a rotary evaporator
  7. filtrationThe resulting brown oil is fractionally filtered through 200 g of silica gel (Merck 0.04-063 mesh) with 1 l of hexane/ethyl acetate (1:1)
  8. concentrationThe ethyl acetate fraction is then concentrated by evaporation on a rotary evaporator

Sources & evidence

ORD record
ord-e8aa4f2db8c644148350068aef6cf368
Source dataset
uspto-grants-2009_12
Patent number
US07632906B2

Reaction notes

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