1-Iodooctane → HCID 85800033, compound

HRID 2367914Notes

Reaction equation

HRID 2367914 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[NH4+].[Cl-]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 123801-IodooctaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Product 1

HCID 85800033HCID 85800033, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 4-(benzyloxy)-3-hydroxybenzaldehyde (190 mg, 0.83 mmol) in anhydrous DMF (2.0 mL) was added 60% NaH (40 mg, 1.00 mmol) at 0° C. followed by the addition of 1-iodooctane (300 mg, 1.25 mmol). The reaction mixture was stirred at room temperature (r.t.) overnight and NH4Cl solution was then added. The mixture was extracted with ethyl acetate 3 times and the combined organic layers were dried and concentrated under vacuum. The resulting residue was purified through flash column chromatography (Hexane:Ethyl Acetate=10:1) to yield 4-(benzyloxy)-3-(octyloxy)benzaldehyde (235 mg, 83%) as light yellow oil, which was subsequently subjected to hydrogenolysis in ethyl acetate in the presence of 10% Pd/C. After filtration and concentration, the crude residue was purified by column chromatography (Hexane:Ethyl Acetate=5:1) to give 3 (125 mg, 72%) as light yellow oil. 1H NMR (CDCl3, 300 MHz) δ 9.80 (s, 1H), 7.36-7.42 (m, 2H), 7.03 (d, J=8.6 Hz, 1H), 6.44 (s, 1H), 4.09 (t, J=6.9 Hz, 2H), 1.82 (hexatet, J=6.7 Hz, 2H), 1.20-1.50 (m, 10H), 0.87 (t, J=6.8 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ 191.09, 151.96, 146.70, 129.90, 127.42, 114.44, 109.68, 69.30, 31.86, 29.37, 29.28, 29.09, 26.03, 22.73, 14.17; ESI-HRMS for [M+H]+ C15H23O3: calcd 251.1647, found 5251.1638.

Workup

  1. additionwas then added
  2. extractionThe mixture was extracted with ethyl acetate 3 times
  3. customthe combined organic layers were dried
  4. concentrationconcentrated under vacuum
  5. customThe resulting residue was purified through flash column chromatography (Hexane:Ethyl Acetate=10:1)

Sources & evidence

ORD record
ord-52ea712aeab24e95b64c78fb342d9e5a
Source dataset
uspto-grants-2014_04
Patent number
US08703437B2

Reaction notes

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