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Sodium Iodide → Ethyl 4-tetradecyloxybenzoate

HRID 235700
Notes
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Reaction equation

HRID 235700 reaction equation
[H-].[Na+].[I-].[Na+].[CH2:5](Br)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=1>CN(C)C=O.O>[CH2:5]([O:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:30][CH:31]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8208Myristyl bromideHCID 8434EthylparabenHCID 24758Sodium hydride

Product 1

HCID 12361481Ethyl 4-tetradecyloxybenzoateYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of about 39.7 g of about 50% sodium hydride, about 13.5 g of sodium iodide and about 208.58 g of tetradecylbromide in about 750 ml of dimethylformamide at about 0° C. was added a solution of about 125 g of ethyl p-hydroxybenzoate in about 400 ml of dimethylformamide over about 1/2 hour. The mixture was stirred at room temperature for about 67 hours and then poured into about 2 liters of water. The solid was collected, washed with water, mixed with hot (about 50° C.) ethyl acetate, washed with water and dried. The solvent was removed and the residue recrystallized from ethanol, giving about 144.57 g of the desired title compound, mp 34°-35° C.

Workup

  1. customThe solid was collected
  2. washwashed with water
  3. additionmixed with hot (about 50° C.) ethyl acetate
  4. washwashed with water
  5. customdried
  6. customThe solvent was removed
  7. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-ff96bc6088034925b47a112f9996e261
Source dataset
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04640913

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes