Acetic Acid → HCID 59514331, compound

HRID 254557Notes

Reaction equation

HRID 254557 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH:16]=[CH2:17])[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2].C(O)(=O)C>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:16][CH3:17])[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59514334HCID 59514334, compound

Product 1

HCID 59514331HCID 59514331, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8-vinyl-naphthalene-1-carboxylic acid ethyl ester (1.1 g) in EtOH (25 ml) was treated with acetic acid (1 ml) and Pd/C (270 mg; 10%) and hydrogenated at normal pressure overnight. The catalyst was filtered off. The filtrate was concentrated. The crude product was isolated by chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 3:2) to give 8-ethyl-naphthalene-1-carboxylic acid ethyl ester (1.05 g) as colorless liquid. MS (ISP): 229.3 ((M+H)+.).

Workup

  1. customhydrogenated at normal pressure overnight
  2. filtrationThe catalyst was filtered off
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was isolated by chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 3:2)

Sources & evidence

ORD record
ord-09d58e4aac8e4058b0b782dec3d869e6
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

Loading…