Sodium Iodide → HCID 12398532, compound

HRID 555799Notes

Reaction equation

HRID 555799 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH2:21](Cl)[C:22]1[CH:29]=[CH:28][C:25]([O:26][CH3:27])=[CH:24][CH:23]=1>CN(C=O)C>[CH3:27][O:26][C:25]1[CH:28]=[CH:29][C:22]([CH2:21][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 12398532HCID 12398532, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of ethyl 4-hydroxybenzoate (530 g, 3.19 mol) in DMF (6 L) were added K2CO3 powder (1102 g, 7.97 mol, 2.5 eq.), NaI (1195 g, 7.97 mol, 2.5 eq.) and PMB-Cl (599.4 g, 3.83 mol, 1.2 eq.) at ambient temperature. The reaction mixture was heated at 50° C. overnight under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and ice-water (9 L) was added to the reaction mixture. The resulting solid was filtered and washed with water (5 L), dried at 40° C. under vacuum to obtain product.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationThe resulting solid was filtered
  3. washwashed with water (5 L)
  4. customdried at 40° C. under vacuum
  5. customto obtain product

Sources & evidence

ORD record
ord-414a411415c9438cb0f38bba4cd6853d
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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