Benzene → 2-(4-Methoxymethoxyphenyl)-5,5-dimethyl-1,3-dioxane

HRID 82743

Reaction equation

HRID 82743 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[OH:13][CH2:14][C:15]([CH3:19])([CH2:17]O)[CH3:16].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1>O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]2[O:13][CH2:14][C:15]([CH3:19])([CH3:17])[CH2:16][O:10]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 31344Neopentyl glycolHCID 2500744-(Methoxymethoxy)benzaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 99429832-(4-Methoxymethoxyphenyl)-5,5-dimethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-methoxymethoxybenzaldehyde, neopentyl glycol (10.3 g, 98.9 mmol), pyridinium para-toluenesulfonate (1.0 g, 3.98 mmol), and benzene (500 ml) was refluxed with azeotropic removal of water for several hours, under argon. The cooled reaction mixture was quenched with 2 ml of triethylamine, and concentrated on rotary evaporator. The product was chromatographed (silica gel, 5% ethyl acetate in hexanes), yielding about 14.83 g of the product.

Workup

  1. customThe cooled reaction mixture
  2. customwas quenched with 2 ml of triethylamine
  3. concentrationconcentrated on rotary evaporator
  4. customThe product was chromatographed (silica gel, 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ffbd58b7353f45b0ba190e0fd9c8f074
Source dataset
uspto-grants-2014_09
Patent number
US08846735B2

Linked notes

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