Methylparaben → HCID 16111873, compound

HRID 252839Notes

Reaction equation

HRID 252839 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.Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

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

Product 1

HCID 16111873HCID 16111873, compoundYield 142%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of methyl 4-hydroxybenzoate 191 (1.08 g, 7.10 mmol) and 4-(2-chloroethyl)morpholine hydrochloride 192 (1.45 g, 7.82 mmol) in acetonitrile was added potassium carbonate (2.95 g, 21.3 mmol). The reaction mixture was heated to 50° C. overnight then cooled to rt and the resulting precipitate was filtered and washed with methanol to provide methyl 4-(2-morpholinoethoxy)benzoate 193 (2.67 g, 142%). 1H NMR: (DMSO) δ (ppm): 400 MHz, (DMSO) d (ppm): 7.87 (s, J=9.0 Hz, 2 h), 7.03 (d, J=9.0 Hz, 2H), 4.15 (t, J=5.7 Hz, 2H), 3.80 (s, 3H), 3.56 (t, J=4.5 Hz, 4H), 2.69 (t, J=5.7 Hz, 4H), 2.47 (m, 4H). MS: 265.13 (calc), 266.1 (obs).

Workup

  1. temperaturethen cooled to rt
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with methanol

Sources & evidence

ORD record
ord-a54c74cb26fe4973ab5a6f2088602474
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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