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

HRID 1866790Notes

Reaction equation

HRID 1866790 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].[CH2:13](O)[CH2:14][CH2:15][OH:16]>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][CH2:14][CH2:13][O:4]1

Participants

4

Reactant 2

HCID 104421,3-PropanediolHCID 23636932-Chloro-1-(2,5-dimethylphenyl)ethan-1-one

Product 1

HCID 160501372-Chloromethyl-2-(2,5-dimethylphenyl)-[1,3]dioxane

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 18.3 g [0.1 mol] of 2-chloro-1-(2,5-dimethylphenyl)ethanone, 15.2 g [0.2 mol] of trimethylene glycol, 1.9 g [0.01 mol] of p-TsOH hydrate and 150 ml of xylene is heated to boiling with a water trap for about 5 hours. Part of the xylene is then distilled off, and the reaction mixture is extracted at room temperature with 30 ml of saturated aqueous NaCl solution and twice with 100 ml of water each time. The organic phase is dried over sodium sulfate and concentrated in vacuo, and all volatiles are distilled off up to about 87° C. under 0.25 mbar. 22.9 g of residue remain with, according to GC, 83.9% product (79.8% of theory).

Workup

  1. temperatureis heated
  2. distillationPart of the xylene is then distilled off
  3. extractionthe reaction mixture is extracted at room temperature with 30 ml of saturated aqueous NaCl solution and twice with 100 ml of water each time
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. distillationall volatiles are distilled off up to about 87° C. under 0.25 mbar

Sources & evidence

ORD record
ord-27cff38d8b52462bb319f8f783d4d036
Source dataset
uspto-grants-2009_12
Patent number
US07629476B2

Reaction notes

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