Water → 2-Chloromethyl-5,5-dimethyl-2-(2,5-dimethylphenyl)-[1,3]dioxane

HRID 2106069Notes

Reaction equation

HRID 2106069 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[CH3:12])=[O:4].[CH3:13][C:14]([CH3:19])([CH2:17]O)[CH2:15][OH:16].O>C1(C)C(C)=CC=CC=1>[Cl:1][CH2:2][C:3]1([C:5]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=2[CH3:12])[O:16][CH2:15][C:14]([CH3:19])([CH3:17])[CH2:13][O:4]1

Participants

5

Reactant 3

HCID 962Water2×HCID 31344Neopentyl glycolHCID 23636932-Chloro-1-(2,5-dimethylphenyl)ethan-1-one

Product 1

HCID 578106312-Chloromethyl-5,5-dimethyl-2-(2,5-dimethylphenyl)-[1,3]dioxane

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

0.5 mol of 2-chloro-1-(2,5-dimethylphenyl)ethanone, 104 g [1 mol] of 2,2-dimethyl-1,3-propanediol (neopentyl glycol) and 9.5 g [0.05 mol] of p-TsOH hydrate are boiled in 500 ml of xylene with a water trap until the formation of water ceases (about 4 hours). 200 ml of water and 30 ml of xylene are added to the reaction mixture at room temperature. A better phase separation is achieved by adding 50 ml of saturated aqueous NaCl solution. The organic phase is then extracted again with 100 ml of water and 100 ml of saturated aqueous NaCl solution, dried and concentrated.

Workup

  1. customA better phase separation
  2. additionby adding 50 ml of saturated aqueous NaCl solution
  3. extractionThe organic phase is then extracted again with 100 ml of water and 100 ml of saturated aqueous NaCl solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f83cf025b1645fa8bb28d366490ccaf
Source dataset
uspto-grants-2009_08
Patent number
US07579500B2

Reaction notes

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