Sodium Iodide → Methyl 4-(tetradecyloxy)benzoate

HRID 484589

Reaction equation

HRID 484589 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.[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH2:25]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7456MethylparabenHCID 8208Myristyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 3312490Methyl 4-(tetradecyloxy)benzoateYield 8.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A well stirred mixture of 100 g of methyl 4-hydroxybenzoate, 182.25 g of tetradecylbromide, 136.26 g of potassium carbonate and 4.93 g of sodium iodide in 1-liter of acetone is refluxed for 48 hours. The mixture is poured into ice water, the solid collected and washed with water. The solid is dissolved in chloroform and washed with 1N sodium hydroxide, dried and evaporated to a residue which is crystallized from hexanes to give 18.5 g of the desired product as a white solid, m.p. 64°-66° C.

Workup

  1. temperatureis refluxed for 48 hours
  2. customthe solid collected
  3. washwashed with water
  4. dissolutionThe solid is dissolved in chloroform
  5. washwashed with 1N sodium hydroxide
  6. customdried
  7. customevaporated to a residue which
  8. customis crystallized from hexanes

Sources & evidence

ORD record
ord-a012738f83fa4824a423cb5d3cec533b
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Linked notes

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