Neopentyl glycol → 4-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanol

HRID 252045Notes

Reaction equation

HRID 252045 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8](=[O:10])[CH3:9])[CH2:4][CH2:3]1.[CH3:11][C:12]([CH2:16]O)([CH2:14][OH:15])[CH3:13]>CC1C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:9][C:8]1([CH:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[O:15][CH2:14][C:12]([CH3:16])([CH3:13])[CH2:11][O:10]1

Participants

5

Reactant 2

HCID 31344Neopentyl glycolHCID 137701531-(4-Hydroxycyclohexyl)ethanone

Product 1

HCID 231479574-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanolYield 62%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-hydroxy-cyclohexyl)-ethanone (2.24 g, 1 eq.), toluene (160 mL), neopentylglycol (1.96 g, 1.2 eq.) and pTsOH (150 mg, 0.05 eq.) in a flask equipped with Dean-Stark apparatus was heated to reflux overnight. The mixture was cooled down to room temperature and concentrated. The crude product was purified by silica gel column chromatography (25% to 50% EtOAc/hexanes) to give 4-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-cyclohexanol (2.23 g, 62%).

Workup

  1. customequipped with Dean-Stark apparatus
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel column chromatography (25% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-449ded45e88b4b8c9e7b7dba4bbea41c
Source dataset
uspto-grants-2011_01
Patent number
US07868002B2

Reaction notes

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