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

HRID 348501Notes

Reaction equation

HRID 348501 reaction equation
Br[C:2](=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH3:12])=[CH:6][CH:5]=1.[CH3:14][CH:15]([CH3:25])CN(C=CC)CC(C)C.S(=O)(=O)(O)O.[OH:31][CH2:32][C:33]([CH3:37])([CH2:35][OH:36])[CH3:34].C1(C)C=CC(S(O)(=O)=[O:45])=CC=1>O.C(#N)C>[CH3:34][C:33]1([CH3:37])[CH2:35][O:36][CH:14]([CH:15]([CH3:25])[CH2:2][C:3]([C:4]2[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH3:12])=[CH:8][CH:9]=2)=[O:45])[O:31][CH2:32]1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 31344Neopentyl glycolHCID 230774532-Bromo-1-(4-ethoxyphenyl)ethan-2-oneHCID 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 483.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

2-Bromo-1-(4-ethoxyphenyl)ethan-2-one (5.0 kg) and N,N-bis(2-methylpropyl)-1-propenylamine (5.1 kg) were added to 20 liters of acetonitrile under an atmosphere of nitrogen and the mixture was stirred at around 50° C. for 1.5 hours. To the reaction mixture were added successively 20 liters of water, 5.0 kg of concentrated sulfuric acid, 3.2 kg of neopentyl glycol, and 0.5 kg of para-toluenesulfonic acid and the mixture was stirred at around 50° C. for 1.5 hours. After cooling the reaction mixture to the room temperature, crystals precipitated. These crystals were isolated by filtration to give 4.3 kg (yield 71%) of the title compound as white crystals.

Workup

  1. stirringthe mixture was stirred at around 50° C. for 1.5 hours
  2. temperatureAfter cooling the reaction mixture to the room temperature, crystals
  3. customprecipitated
  4. customThese crystals were isolated by filtration

Sources & evidence

ORD record
ord-bad89eb290ee41aeb006f8439f8aaf19
Source dataset
uspto-grants-2007_02
Patent number
US07176323B2

Reaction notes

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