Water → HCID 23052170, compound

HRID 1650634Notes

Reaction equation

HRID 1650634 reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:7])=[CH:4][CH:3]=1.[C:23]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)(=[O:25])[CH3:24].O>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:23]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:7])=[CH:21][CH:22]=2)=[O:32])=[CH:29][CH:28]=1)(=[O:25])[CH3:24]

Participants

6

Reactant 3

HCID 962WaterHCID 17569Benzoic acid, 4-hydroxy-, dodecyl esterHCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 23052170HCID 23052170, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

In pyridine was dissolved 5 g of dodecyl p-hydroxybenzoate, and a solution of 5 g of p-acetoxybenzoic acid chloride in chloroform was added dropwise to the solution and the mixture was stirred at room temperature for 4 hours. Water was added to the thus-obtained solution, 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, dehydrated on anhydrous magnesium sulfate and concentrated. The concentrate was recrystallized from a mixed solvent of n-hexane and ethyl acetate to obtain 3.18 g dodecyl 4-(4-acetoxybenzoyloxy)benzoate. The obtained ester was dissolved in a mixed solvent of tetrahydrofuran and methanol at a volume ratio of 10/1, 7 ml of a 1N aqueous solution of lithium hydroxide was added to the solution, and the obtained mixture was stirred at room temperature for 1 hour, diluted with ethyl acetate and washed with a saturated aqueous solution of sodium chloride. Then, the liquid was dried on anhydrous magnesium sulfate and concentrated, and the concentrate was recrystallized from a liquid mixture of n-hexane and ethyl acetate to obtain 2.22 g of dodecyl 4-(4-hydroxybenzoyloxy)benzoate.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washthe extract was washed with a 0.5N aqueous solution of hydrochloric acid
  3. concentrationconcentrated
  4. customThe concentrate was recrystallized from a mixed solvent of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-67c8e433cced46c3bc3301d6c809f144
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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