Dimethyl Sulfoxide → Methanone, [2-hydroxy-4-(3-hydroxypropoxy)phenyl]phenyl-

HRID 1862182Notes

Reaction equation

HRID 1862182 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Cl[CH:18]([OH:21])[CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>[I-].[K+].O>[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH2:20][CH2:19][CH2:18][OH:21])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 85722,4-DihydroxybenzophenoneHCID 11430Potassium CarbonateHCID 151098631-Chloropropan-1-ol

Product 1

HCID 10945581Methanone, [2-hydroxy-4-(3-hydroxypropoxy)phenyl]phenyl-Yield 76.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

To a 250 mL 3-necked round-bottom flask equipped with a magnetic stirrer was charged 20 g (93.5 mmol) of 2,4-dihydroxybenzophenone, 8.8 g (93.5 mmol) of chloropropanol, 100 mg (0.6 mmol) of potassium iodide, 12.92 g (93.5 mmol) of potassium carbonate, and 100 mL of dimethyl sulfoxide. The flask was immersed in an oil bath and the mixture heated at a bath temperature of 125° C. for 14 hours. The mixture was poured into 1.4 L of water and extracted with four 500 mL portions of methylene chloride. The combined organic extracts were washed with five 1200 in L portions of water, followed by two 2 L portions of 0.025% aqueous NaOH, and another 1.2 L portion of water. The organic layer was dried (MgSO4), filtered through Celite, and concentrated, leaving 19.4 g of product as a yellow solid. 1H NMR (CDCl3): δ12.58 (s, 1H, ArOH); 7.60-7.35 (m, 6H, Ar—H); 6.45-6.30 (m, 2H, Ar—H); 4.10 (t, 2H, Ar—O—CH2—); 3.79 (t, 2H, H—O—CH2—); 1.99 (m, 2H, —CH2—CH2—CH2—).

Workup

  1. customTo a 250 mL 3-necked round-bottom flask equipped with a magnetic stirrer
  2. customThe flask was immersed in an oil bath
  3. extractionextracted with four 500 mL portions of methylene chloride
  4. washThe combined organic extracts were washed with five 1200 in L portions of water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered through Celite
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2d99d51e0dd14ad8bc03383d2d551250
Source dataset
uspto-grants-2003_03
Patent number
US06537670B1

Reaction notes

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