HCID 67163380, compound → HCID 53804428, compound

HRID 68644Notes

Reaction equation

HRID 68644 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1>CO.[C].[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 67163380HCID 67163380, compound

Product 1

HCID 53804428HCID 53804428, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In a solution of the compound 29 (2.50 g) in methanol (30 mL), 10% palladium carbon (250 mg) was added under an argon atmosphere. The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 3 hours. The reaction mixture was filtered with Celite (trade name) and the filtrate was concentrated. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=7:3→3:7) to obtain methyl 4-(6-hydroxyhexyl)benzoate (2.22 g). The same procedure as a series of reactions of Example 25 was carried out, except that methyl 4-(6-hydroxyhexyl)benzoate was used in place of the compound 24, to obtain the title compound having the following physical properties.

Workup

  1. filtrationThe reaction mixture was filtered with Celite (trade name)
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=7:3→3:7)

Sources & evidence

ORD record
ord-963bdf7e9a0849a5b19f9213ba9bec6e
Source dataset
uspto-grants-2014_09
Patent number
US08822459B2

Reaction notes

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