HCID 23052170, compound → HCID 23052152, compound

HRID 1650635Notes

Reaction equation

HRID 1650635 reaction equation
C([O:4][C:5]1[CH:34]=[CH:33][C:8]([C:9]([O:11][C:12]2[CH:32]=[CH:31][C:15]([C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:17])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)(=O)C>O1CCCC1.CO.[OH-].[Li+].C(OCC)(=O)C>[OH:4][C:5]1[CH:34]=[CH:33][C:8]([C:9]([O:11][C:12]2[CH:32]=[CH:31][C:15]([C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:17])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1

Participants

6

Reactant 1

HCID 23052170HCID 23052170, compound

Product 1

HCID 23052152HCID 23052152, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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. additionwas added to the solution
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. dry with materialThen, the liquid was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe concentrate was recrystallized from a liquid mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-29d582cf10ce4f85b5243000e23801e7
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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