Water → HCID 23052162, compound

HRID 1650633Notes

Reaction equation

HRID 1650633 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:17]([O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)(=[O:19])[CH3:18].O>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:17]([O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([O:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][CH:12]=2)=[O:26])=[CH:23][CH:22]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 77412Phenol, 4-(octyloxy)-HCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 23052162HCID 23052162, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

In pyridine was dissolved 2 g of p-octyloxyphenol, and a solution of p-acetoxybenzoic acid chloride in chloroform was added dropwise to the thus-obtained solution and the mixture was stirred at room temperature for 3 hours. Water was added to the thus-obtained solution and the mixture was extracted with chloroform, and the extract was washed with a 0.5N aqueous solution of hydrochloric acid, a saturated aqueous solution of sodium chloride, a saturated aqueous solution of NaHCO3 and a saturated aqueous solution of sodium chloride in succession, followed by concentration. The concentrate was recrystallized from n-hexane to obtain 2.35 g of 4-octyloxyphenyl 4-acetoxybenzoate. The product was dissolved in a liquid mixture comprising tetrahydrofuran and methanol at a volume ratio of 10/1, 6.2 ml of a 1N aqueous solution of lithium hydroxide was added to the solution, the mixture was stirred at room temperature for 1 hour, and the mixture was diluted with ethyl acetate and washed with a saturated aqueous solution of sodium chloride. Then, the liquid was dehydrated on anhydrous magnesium sulfate and concentrated, and the concentrate was recrystallized from ethyl acetate to obtain 1.1 g of 4-octyloxyphenyl 4-hydroxybenzoate.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washthe extract was washed with a 0.5N aqueous solution of hydrochloric acid
  3. concentrationa saturated aqueous solution of sodium chloride, a saturated aqueous solution of NaHCO3 and a saturated aqueous solution of sodium chloride in succession, followed by concentration
  4. customThe concentrate was recrystallized from n-hexane

Sources & evidence

ORD record
ord-389ad4f3001b4f0e830d4c40c0a262ee
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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