Neopentyl glycol → 3-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-ethoxyphenyl)butan-1-one

HRID 348502Notes

Reaction equation

HRID 348502 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[CH:7][CH:6]=1)=[O:4].[CH3:14][CH:15](C)[CH2:16]N(C=CC)CC(C)C.CC(N(C)C)=O.[OH:32][CH2:33][C:34]([CH3:38])([CH2:36][OH:37])[CH3:35]>O>[CH3:35][C:34]1([CH3:38])[CH2:36][O:37][CH:14]([CH:15]([CH3:16])[CH2:2][C:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[CH:7][CH:6]=2)=[O:4])[O:32][CH2:33]1

Participants

6

Reactant 4

HCID 31344Neopentyl glycolHCID 31374DimethylacetamideHCID 21130602-Bromo-1-(4-ethoxyphenyl)ethanoneHCID 54063094N,N-Bis(2-methylpropyl)prop-1-en-1-amine

Product 1

HCID 117226983-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-ethoxyphenyl)butan-1-oneYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Bromo-1-(4-ethoxyphenyl)ethan-1-one (4.0 g) and N,N-bis(2-methylpropyl)-1-propenylamine (4.0 g) were added to 16 ml of dimethylacetamide under an atmosphere of nitrogen and the mixture was stirred between 50° C. and 55° C. for 2 hours. To the reaction mixture were added successively 1.6 g of paratoluenesulfonic acid and 2.1 g of neopentyl glycol and the mixture was stirred between 50° C. and 60° C. for 3 hours. After addition of 8 ml of water to the reaction mixture and cooling the reaction mixture to the room temperature, crystals precipitated. These crystals were isolated by filtration to give 3.7 g (yield 74%) of the title compound as white crystals. The 1H-NMR spectrum of the product is substantially identical with that of the product of Example 1.

Workup

  1. stirringthe mixture was stirred between 50° C. and 60° C. for 3 hours
  2. customprecipitated
  3. customThese crystals were isolated by filtration

Sources & evidence

ORD record
ord-5047eab9b91a4888887c1f259dbfd8e3
Source dataset
uspto-grants-2007_02
Patent number
US07176323B2

Reaction notes

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