N,N-Dimethylaniline → HCID 19880043, compound

HRID 1885120Notes

Reaction equation

HRID 1885120 reaction equation
[CH2:1]([O:6][CH:7]([CH3:11])[CH2:8][CH2:9][OH:10])[CH2:2][CH2:3][CH2:4][CH3:5].CN(C)C1C=CC=CC=1.CCOCC.[C:26]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)(=[O:28])[CH3:27]>O>[C:26]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([O:10][CH2:9][CH2:8][CH:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH3:11])=[O:35])=[CH:32][CH:31]=1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 3283Diethyl EtherHCID 2756254p-Acetoxybenzoyl chlorideHCID 19880018HCID 19880018, compound

Product 1

HCID 19880043HCID 19880043, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Separately, 9.0 g of 3-pentyloxybutanol and 6.82 g of N,N-dimethylaniline were added to 20 ml of ether, and under stirring at room temperature, 11.5 g p-acetyloxybenzoic acid chloride was added thereto dropwise. Then, the mixture was heat-refluxed for 3.5 hours. The crystal was dissolved by adding 50 ml of water and extracted with ether. The ether layer was washed successively with 10% H2SO4 aqueous solution and water and dried with anhydrous Na2SO4, followed by distilling-off of the solvent to obtain 17.5 g of 4-(3-pentyloxybutoxycarbonyl)phenyl acetate.

Workup

  1. temperatureThen, the mixture was heat-refluxed for 3.5 hours
  2. dissolutionThe crystal was dissolved
  3. extractionextracted with ether
  4. washThe ether layer was washed successively with 10% H2SO4 aqueous solution and water
  5. dry with materialdried with anhydrous Na2SO4

Sources & evidence

ORD record
ord-8c29a76fad6c44228c9f3a86f2d9ef1b
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

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