Potassium Carbonate → 3,5-Diphenyl4-[(2-methoxyethoxy)methoxy]-phenyl decyl ether

HRID 1281436

Reaction equation

HRID 1281436 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([OH:26])[CH:10]=[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]=2[O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>CN(C=O)C>[CH2:34]([O:26][C:9]1[CH:10]=[C:11]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:12]([O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=1)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 163141-Iododecane2×HCID 222375693,5-Diphenyl-4-[(2-methoxyethoxy)methoxy]-phenol

Product 1

HCID 222374833,5-Diphenyl4-[(2-methoxyethoxy)methoxy]-phenyl decyl etherYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
63 °C

Procedure

To a stirred solution of 3,5-diphenyl-4-[(2-methoxyethoxy)methoxy]-phenol (0.946 g, 2.7 mmol) in DMF (15ml) was added K2CO3 (0.746 g, 5.4 mmol) and iododecane (1.632 g, 5.4 mmol). The reaction mixture was warmed to ˜63° C. After ˜20 h, additional K2CO3 (0.373 g, 2.7 mmol) and iododecane (0.816 g, 2.7 mmol) were added. Heating was continued for an additional 20 h followed by stirring at room temperature for 20 h. The reaction mixture was concentrated in vac and the residue taken up in EtOAc (50 ml) and water (20 ml). The layers were shaken and separated and the organic layer was washed with water (3×10 ml), brine (2×10 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (hexane and 5% EtOAc/Hex) to give the product as a brown oil (0.897 g, 68%); 1H NMR (400 MHz, DMSO-d6) δ 0.83-0.88 (m, 3H), 1.20-1.37 (m, 12H), 1.37-1.46 (m, 2H), 1.68-1.76 (m, 2H), 2.71-2.75 (m, 2H), 2.86-2.88 (m, 2H), 3.01 (s, 3H), 4.03 (t, J=6.4 Hz, 2H), 4.22 (s, 2H), 6.87 (s, 2H), 7.34-7.39 (m, 2H), 7.42-7.48 (m, 4H), 7.56-7.60 (m, 4H); IR (film) 2940, 1590, 1460, 1190 cm−1; mass spectrum [(+)ESI], m/z 508 (M+NH4)+.

Workup

  1. temperatureHeating
  2. waitwas continued for an additional 20 h
  3. concentrationThe reaction mixture was concentrated in vac
  4. stirringThe layers were shaken
  5. customseparated
  6. washthe organic layer was washed with water (3×10 ml), brine (2×10 ml)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vac
  10. customdried
  11. customThe residue was purified by flash chromatography (hexane and 5% EtOAc/Hex)

Sources & evidence

ORD record
ord-f2b8359d64564c94b8d7eb6b6bc0ad0b
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Linked notes

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