Water → HCID 16111873, compound

HRID 567097Notes

Reaction equation

HRID 567097 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.O>CN(C)C=O.C(OCC)(=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

7

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 16111873HCID 16111873, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-hydroxybenzoate (10 g, 66 mmoles) was dissolved in N,N-dimethylformamide (200 mL). Potassium carbonate (45 g, 0.33 moles) and 4-(2-chloroethyl)morpholine hydrochloride (18.3 g, 99 mmoles) were added and the resulting mixture was stirred vigorously at room temperature for 5 days. The reaction mixture was poured into water (500 mL) and extraction with ethyl acetate (2×250 mL), washing of the combined organic phases with water (200 mL), drying over MgSO4 and evaporation afforded 16.8 g (96%) of methyl 4-(2-morpholin-4-ylethoxy)benzoate as an oil.

Workup

  1. washwashing of the combined organic phases with water (200 mL)
  2. dry with materialdrying over MgSO4 and evaporation

Sources & evidence

ORD record
ord-68abad0811b24fb786c3075ce8ef566a
Source dataset
uspto-grants-2001_01
Patent number
US06177443B1

Reaction notes

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