Hydrochloric Acid → HCID 855016, compound

HRID 2059353Notes

Reaction equation

HRID 2059353 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8](=[O:11])([O-])[O-].[K+].[K+].C[CH2:15][O:16]CC.Cl.[CH3:20]N(C)C=O>CC(C)=O.[I-].[K+]>[O:7]([CH2:20][C@H:8]([OH:11])[CH2:15][OH:16])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 996PhenolHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 11430Potassium Carbonate

Product 1

HCID 855016HCID 855016, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 110 g (0.384 mol) of (R)-2,3-O-isopropylidene-1-O-tuluenesulfonyl-1,2,3-trihydroxypropane (J. J. Baldwin, A. W. Raab, K. Mensler, B. H. Arison, D. E. McClure, J. Org. Chem., 43, 4876 (1978)), 72.3 g (0.768 mol) of phenol, 106.2 g (0.768 mol) of potassium carbonate, and 1.0 g (0.007 mole) of potassium iodide in 400 ml of dry dimethylformamide was heated under nitrogen at 100°-110° for 5 hours. After cooling to room temperature, 600 ml of ether was added, the slurry filtered and the filtrate washed with water, brine, and dried over anhydrous magnesium sulfate. Removal of the drying agent by filtration followed by isolation in vacuo afforded an oil which was refluxed in 80 ml of acetone and 240 ml of 1N hydrochloric acid for 30 minutes. The acetone was removed in vacuo, the aqueous solution extracted with 3×200 ml of ethyl acetate and the combined organic layers washed with 1 N sodium hydroxide (200 ml), water (200 ml), brine (200 ml) and dried over anhydrous magnesium sulfate. On removal of the drying agent by filtration the solvent was removed in vacuo to afford an oil, which solidified on standing. Crystallization from ethyl acetate/petroleum ether afforded 29.8 g (51%) of the title compound: mp 64°-65°; [α]24D -8.88° (1,.5,CHCl3); 1H-nmr (CDCl3) δ 7.50-6.81 (m,5), 4.31-3.89 (m,1), 4.01 (s,2,OH), 3.89-3.57 (m,4); ir (KBr) cm-1 3425 (s,OH).

Workup

  1. filtrationthe slurry filtered
  2. washthe filtrate washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customRemoval of the drying agent
  5. filtrationby filtration
  6. customafforded an oil which
  7. customThe acetone was removed in vacuo
  8. extractionthe aqueous solution extracted with 3×200 ml of ethyl acetate
  9. washthe combined organic layers washed with 1 N sodium hydroxide (200 ml), water (200 ml), brine (200 ml)
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customOn removal of the drying agent
  12. filtrationby filtration the solvent
  13. customwas removed in vacuo
  14. customto afford an oil, which
  15. customCrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-55b34fb5e6984be6896b6c61726e7d07
Source dataset
uspto-grants-1982_03
Patent number
US04322557

Reaction notes

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