Water → 9-(2-Hydroxyethyl)-7, 11-dioxaspiro[5,5]undecane

HRID 2354Notes

Reaction equation

HRID 2354 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:14][CH2:13][O:12][C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[O:5][CH2:4]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[OH:12][CH2:13][CH2:14][CH:3]1[CH2:2][O:1][C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[O:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 110308447,12-Dioxaspiro[5.6]dodecane-9-methanol

Product 1

HCID 108673469-(2-Hydroxyethyl)-7, 11-dioxaspiro[5,5]undecane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 9-hydroxymethyl-7, 12-dioxaspiro[5,6]dodecane of the formula V (4 g) of the drawings in benzene (15 ml) was stirred at 10° C. for 5 hr with anhydrous p-toluenesulphonic acid (0.2 g). The reaction mixture was made alkaline by adding TEA and water. The benzene layer was separated and the aqueous layer extracted with benzene. The combined benzene solution was dried over K2CO3 and evaporate to a residue (4 g). It was chromatograped on silicagel using chloroform-methanol mixture as eluent to give 9-(2-hydroxyethyl)-7, 11-dioxaspiro[5,5]undecane of formula VI (2.8 g) (70%) of the drawings as colorless viscous liquid.

Workup

  1. customThe benzene layer was separated
  2. extractionthe aqueous layer extracted with benzene
  3. dry with materialThe combined benzene solution was dried over K2CO3
  4. customevaporate to a residue (4 g)

Sources & evidence

ORD record
ord-41c36e816c8a49348cb7de1b22c2c650
Source dataset
uspto-grants-1998_03
Patent number
US05728848

Reaction notes

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