Methylparaben → HCID 684101, compound

HRID 392820Notes

Reaction equation

HRID 392820 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][O:11][C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 96024-Fluorobenzyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 684101HCID 684101, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl p-hydroxybenzoate (4.38 g, 28.8 mmol), p-fluorobenzyl chloride (5.0 g, 34.6 mmol) and anhydrous potassium carbonate (10 g) in acetone (250 ml) was heated under reflux for 24 h. The solid was then filtered and the filtrate was evaporated under reduced pressure. Crystallization of the residue from hexane gave 7.20 g (96%) of the title ester as white plates: mp 93-94° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.9 (3H, s, OCH3), 5.1 (2H, s, CH2), 7.0 (2H, d, J=8.8 Hz, aromatics), 7.11 (2H, m, aromatics), 7.43 (2 H, m, aromatics), 8.02 (2H, d, J=8.8 Hz, aromatics). Anal. Calcd for C15H13FO3: C, 69.22; H, 5.03. Found: C, 68.89; H, 4.69.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. filtrationThe solid was then filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customCrystallization of the residue from hexane

Sources & evidence

ORD record
ord-549a5c48b39047a0aa466c1dc9d8978a
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Reaction notes

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