Ethylene Glycol → 2-[(Benzyloxy)methyl]-5,8-dioxaspiro[3.4]octane

HRID 1966813Notes

Reaction equation

HRID 1966813 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][CH2:20][CH:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:26](O)[CH2:27][OH:28].O>C1C=CC=CC=1>[CH2:12]([O:19][CH2:20][CH:21]1[CH2:24][C:23]2([O:28][CH2:27][CH2:26][O:25]2)[CH2:22]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 118198503-((Benzyloxy)methyl)cyclobutanone

Product 1

HCID 120735822-[(Benzyloxy)methyl]-5,8-dioxaspiro[3.4]octane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Toluene sulphonic acid (2.0 gm) was added to a solution of 3-[(benzyloxy)methyl]cyclobutanone (25.0 gm, 131.6 mmol) (step b) and 1,2-ethanediol (8.98 gm, 144.7 mmol) in benzene and the reaction mixture was refluxed with removal of water through dean-stark apparatus. After about 6 hours, the reaction mixture was cooled to room temperature and washed with saturated sodium bicarbonate solution, followed by water and brine. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to get a crude product, which was purified by column chromatography.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b23567b64d20417a92136be82466d129
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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