Methylparaben → HCID 16111873, compound

HRID 2218382Notes

Reaction equation

HRID 2218382 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>CN(C=O)C>[N:22]1([CH2:21][CH2:20][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 16111873HCID 16111873, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 4-hydroxybenzoate (40 g, 260 mmol) was dissolved in DMF (300 ml), K2CO3 (90 g, 650 mmol) was added and heated to 100° C. 4-(2-Chloroethyl)morpholine hydrochloride (53 g, 280 mmol) was added slowly (35 min) to the slurry. After 2 h at 100° C., the solid was removed by filtration and the solution was evaporated in vacuo. The residue was dissolved in EtOAc and washed with aqueous NaHCO3, brine and dried (Na2SO4) to give the pure product as a white powder in quantitative yield.

Workup

  1. customthe solid was removed by filtration
  2. customthe solution was evaporated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with aqueous NaHCO3, brine
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-500a91bded6740f9b0edb77cc9d3182b
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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