9-(2-Furyl)-8-nonenoic acid → 9-(2-furyl)nonanoic Acid

HRID 1004473Notes

Reaction equation

HRID 1004473 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]>[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

3

Reactant 1

HCID 541079749-(2-Furyl)-8-nonenoic acid

Product 1

HCID 101768929-(2-furyl)nonanoic AcidYield 93.6%

Reagents, catalysts & solvents 1

HCID 16218511Pd barium sulfateCatalyst

Procedure

This compound was synthesized from 9-(2-furyl)-8-nonenoic acid (0.89 g, 4 mmol) by a hydrogenation reaction using Pd/BaSO4 (90 mg). Crystallization (petroleum ether) afforded the product (0.84 g, 93%) as white crystals (mp 31-32° C.); IR: 3450-2500, 1720 cm-1 ; 1H-NMR: 1.30 (m, 8H), 1.63 (m, 4H), 2.35 (t, 2H), 2.60 (t, 2H), 5.95 (s, 1H), 6.27 (s, 1H), 7.28 (s, 1H), 9.85 (bs, 1H). Anal. Calcd. for C13H20O3 : C, 69.61, H, 8.99%; Found: C, 69.42, H, 9.04%.

Workup

  1. customCrystallization (petroleum ether)

Sources & evidence

ORD record
ord-167bdbc07a2041bfaadd1f678530bf20
Source dataset
uspto-grants-2000_04
Patent number
US06048989

Reaction notes

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