p-Toluenesulfonic acid → HCID 89525931, compound

HRID 2204445Notes

Reaction equation

HRID 2204445 reaction equation
[CH2:1]([O:3][CH:4]([O:11][CH2:12][CH3:13])[C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[CH3:8])C.C(O)CCO.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[O:3]1[CH2:1][CH2:13][CH2:12][O:11][CH:4]1[C:5](=[O:10])[CH:6]=[C:7]([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 516892Sodium BicarbonateHCID 79496236HCID 79496236, compound

Product 1

HCID 89525931HCID 89525931, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1b (1.02 g, 5.49 mmol) and 1,3-propanediol (0.600 mL, 8.23 mmol) in benzene (10.8 mL) was treated with p-toluenesulfonic acid (522 mg, 2.75 mmol). The reaction mixture was stirred at 80° C. for 4.5 h. Saturated aqueous NaHCO3 was added, and the mixture was extracted with Et2O. The organic extract was washed (water), dried (Na2SO4), concentrated to a brown liquid, and chromatographed [silica, hexanes/EtOAc (5:1)] to afford a yellow liquid (600 mg, 64%): 1H NMR δ 1.40-1.45 (m, 1H), 1.96 (s, 3H), 2.20 (s, 3H), 2.12-2.25 (m, 1H), 3.83-3.92 (m, 2H), 4.20-4.26 (m, 2H), 4.79 (s, 1H), 6.42 (s, 1H); 13C NMR δ 21.7, 25.9, 28.5, 67.3, 101.4, 119.0, 161.2, 192.1; ESI-MS obsd 193.0833, calcd 193.0835 [(M+Na)+, M=C9H14O3].

Workup

  1. extractionthe mixture was extracted with Et2O
  2. extractionThe organic extract
  3. washwas washed (water)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a brown liquid
  6. customchromatographed [silica, hexanes/EtOAc (5:1)]

Sources & evidence

ORD record
ord-0111a189036047b38e000368cee352e1
Source dataset
uspto-grants-2016_06
Patent number
US09365722B2

Reaction notes

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