p-Toluenesulfonic acid monohydrate → HCID 57554681, compound

HRID 1511895Notes

Reaction equation

HRID 1511895 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:21])[CH2:16][CH:17]([OH:20])[CH2:18]O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O.CCCCCCC>ClCCCl>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[O:21][CH2:18][CH:17]([OH:20])[CH2:16]2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21899848Ethylacetate heptaneHCID 57554761HCID 57554761, compound

Product 1

HCID 57554681HCID 57554681, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

4-(4-octylphenyl)butane-1,2,4-triol (12 g, 40.6 mmol) was dissolved in 1,2-Dichloroethane (815 ml) under nitrogen. p-Toluenesulfonic acid monohydrate (1.55 g, 8.2 mmol) (TCI) was added and the reaction heated at about 50° C. for about 3 h. TLC in 1:1 EtOAc/heptane showed (PMA visualization) reaction complete. The solution was washed with saturated sodium bicarbonate and extract with methylene chloride (2×). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated to a yellow oil. The resulting oil was chromatographed on 330 g redi-sep column eluting with 20% EtOAc in heptane for 10 min ramping to 50% over 20 min and then holding at 50% until all the product was off (monitor at 223 nm due to weak chromaphore at longer wavelengths). Removed solvent under reduced pressure to provide 5-(4-octylphenyl)tetrahydrofuran-3-ol (7.36 g, 26.6 mmol, 73.3% yield) as a colorless oil: LC/MS (method A) Rt=3.76 min.; MS m/z: 277.15 (M+H)+.

Workup

  1. custom(PMA visualization) reaction complete
  2. washThe solution was washed with saturated sodium bicarbonate
  3. extractionextract with methylene chloride (2×)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to a yellow oil
  8. customThe resulting oil was chromatographed on 330 g redi-sep column
  9. washeluting with 20% EtOAc in heptane for 10 min

Sources & evidence

ORD record
ord-3afaf30667084466b4316290c2cfe397
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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