Hydrochloric Acid → 1-Octanol, 8-[(tetrahydro-2H-pyran-2-yl)oxy]-

HRID 974736Notes

Reaction equation

HRID 974736 reaction equation
[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.Cl.C([O-])(O)=O.[Na+]>ClCCl>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 694201,8-OctanediolHCID 516892Sodium Bicarbonate

Product 1

HCID 109772951-Octanol, 8-[(tetrahydro-2H-pyran-2-yl)oxy]-Yield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneCatalyst

Procedure

1,8-Octanediol (16.8 g) (115 mmol) and 4.83 g of dihydropyran (57.5 mmol) in 1400 ml of dichloromethane containing 5 drops of concentrated HCl were stirred for 2 hours. Then 10 g of NaHCO3 were stirred in and the solution was filtered. Dichloromethane was removed with a rotary evaporator, and the resulting residue was triturated with pentane; the undissolved solid was 1,8-octanediol. The solid was filtered from the pentane solution, and the pentane was removed with a rotary evaporator to give 13.2 g (99.8%) of crude product oil.

Workup

  1. filtrationwas filtered
  2. customDichloromethane was removed with a rotary evaporator
  3. customthe resulting residue was triturated with pentane
  4. filtrationThe solid was filtered from the pentane solution
  5. customthe pentane was removed with a rotary evaporator

Sources & evidence

ORD record
ord-cbd1087467f84a729bd205d294d56e0c
Source dataset
uspto-grants-1997_03
Patent number
US05607670

Reaction notes

Loading…