1,4-Dioxane → Ethyl 11-(p-hydroxyphenoxy)undecanoate

HRID 634596Notes

Reaction equation

HRID 634596 reaction equation
C([O:8][C:9]1[CH:30]=[CH:29][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:11][CH:10]=1)C1C=CC=CC=1.O1CCOCC1.[H][H]>[C].[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 21259961Ethyl 11-(p-benzyloxyphenoxy)undecanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 21260204Ethyl 11-(p-hydroxyphenoxy)undecanoateYield 93.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

In a 1000 ml pressure resistant flask equipped with a stirrer were charged 100.0 g of ethyl 11-(p-benzyloxyphenoxy)undecanoate synthesized in Synthetic example 1, 3.0 g of a 10% palladium-carbon, 400 ml of 1,4-dioxane and 200 ml of ethanol, and the mixture was heated to 60° C. and under pressurized conditions of an inner vessel pressure at 2.5 kgf/cm2, a hydrogen gas was passed through and the mixture was vigorously stirred for 3 hours. Insolubles were removed by filtration, and the filtrate was concentrated to precipitate crystals. The resulting crystals were washed with cooled n-hexane to obtain 73.4 g of the title compound.

Workup

  1. customIn a 1000 ml pressure resistant flask equipped with a stirrer
  2. customInsolubles were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customto precipitate crystals
  5. washThe resulting crystals were washed with cooled n-hexane

Sources & evidence

ORD record
ord-3773137e695c4665af66681da06d780e
Source dataset
uspto-grants-2001_02
Patent number
US06184180B2

Reaction notes

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