Ethylene Glycol → HCID 66776924, compound

HRID 2387698Notes

Reaction equation

HRID 2387698 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:10])[CH2:8][OH:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCl>O>[O:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]1[O:9][CH2:8][CH2:7][OH:10]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 66776924HCID 66776924, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,4-Dihydro-2H-pyran (30.0 g, 0.36 mol), ethylene glycol (310.0 cm3, 5.36 mol) and p-toluene sulphonic acid (ca. 1 mol %, catalyst) were added to dichloromethane (100 cm3) and the mixture stirred at ambient temperature for 18 hours under an inert gas atmosphere. Water (ca. 150 cm3) was then added, resulting in a biphasic mixture. The organic phase (containing the desired product) was collected and the aqueous phase (containing excess ethylene glycol) extracted with further portions of dichloromethane (3×50 cm3). The combined organic phase and washings were dried over anhydrous magnesium sulphate, filtered and solvent removed in vacuo to yield the crude product containing, almost exclusively, the mono-protected alcohol. The desired product was isolated via flash column chromatography (using silica gel 60 and a 3:1 ratio of hexane:ethyl acetate as eluant). Yield=9.10 g (17.3%).

Workup

  1. customresulting in a biphasic mixture

Sources & evidence

ORD record
ord-b33101a07f5d4e0e976d60264f54fdba
Source dataset
uspto-grants-2012_09
Patent number
US08268959B2

Reaction notes

Loading…