HCID 23052149, compound → HCID 23052148, compound

HRID 1650649Notes

Reaction equation

HRID 1650649 reaction equation
[CH2:1]([O:13][C:14]1[CH:36]=[CH:35][C:17]([C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]([O:27]CC3C=CC=CC=3)=[CH:23][CH:22]=2)=[O:19])=[CH:16][C:15]=1[Cl:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:13][C:14]1[CH:36]=[CH:35][C:17]([C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[O:19])=[CH:16][C:15]=1[Cl:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 23052149HCID 23052149, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23052148HCID 23052148, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 1.0 g of this 4-n-dodecyloxy-3-chlorobenzoic acid was added 10 g of thionyl chloride, and the mixture was refluxed for 3 hours and unreacted thionyl chloride was removed under a reduced pressure. Thus, 4-n-dodecyloxy-3-chlorobenzoic acid chloride was quantitatively obtained. A solution of the so-obtained compound in toluene was added dropwise to a solution of 0.59 g of p-benzyloxyphenol and 0.3 g of triethylamine in toluene, and the mixture was stirred overnight. The thus-obtained solution was diluted with ethyl acetate, and the dilution was washed with 0.5N hydrochloric acid, a saturated aqueous solution of sodium chloride, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in succession, dehydrated on anhydrous sodium sulfate and concentrated under a reduced pressure to obtain p-benzyloxyphenyl 4-dodecyloxy-3-chlorobenzoate. The so-obtained ester was dissolved in ethyl acetate and 1 g of 5%-Pd/C was added to the solution, and the mixture was stirred at room temperature under a pressure of 3 atmospheres in a hydrogen atmosphere for three days and three nights. The Pd/C was removed by filtration and the filtrate was recrystallized from n-hexane to obtain 500 mg of 4-hydroxyphenyl 4-dodecyloxy-3-chlorobenzoate.

Workup

  1. customThe Pd/C was removed by filtration
  2. customthe filtrate was recrystallized from n-hexane

Sources & evidence

ORD record
ord-1206233e8b8542c495a0c491d5bc52ad
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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