Ethylene Glycol → 4-[(2-Methyl-1,3-dioxolan-2-yl)methoxy]phenol

HRID 2082078Notes

Reaction equation

HRID 2082078 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:13](O)[CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:9][C:8]1([CH2:7][O:6][C:5]2[CH:11]=[CH:12][C:2]([OH:1])=[CH:3][CH:4]=2)[O:15][CH2:14][CH2:13][O:10]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 137920581-(4-Hydroxyphenoxy)propan-2-one

Product 1

HCID 197795284-[(2-Methyl-1,3-dioxolan-2-yl)methoxy]phenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(4-hydroxyphenoxy)propan-2-one (3.2 g), 1,2-ethanediol (3.0 ml) and p-toluenesulphonic acid (50 mg) in toluene (100 ml) was stirred under reflux in a Dean and Stark apparatus for 3 1/2 hours in an atmosphere of argon. The reaction mixture was cooled, washed with 5% aqueous sodium bicarbonate (100 ml), washed with water (2×50 ml), washed with brine (50 ml) and dried. Toluene was removed under reduced pressure to give 4-[(2-methyl-1,3-dioxolan-2-yl)methoxy]phenol as an oil (3.4 g).

Workup

  1. temperatureunder reflux in a Dean and Stark apparatus for 3 1/2 hours in an atmosphere of argon
  2. temperatureThe reaction mixture was cooled
  3. washwashed with 5% aqueous sodium bicarbonate (100 ml)
  4. washwashed with water (2×50 ml)
  5. washwashed with brine (50 ml)
  6. customdried
  7. customToluene was removed under reduced pressure

Sources & evidence

ORD record
ord-7166d0f7eaa04f5b96db8e522cd300ff
Source dataset
uspto-grants-1993_02
Patent number
US05187190

Reaction notes

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