Terephthalaldehyde → 4-(1-Hydroxynon-1-yl)benzaldehyde

HRID 898194Notes

Reaction equation

HRID 898194 reaction equation
[CH:1]1[C:6]([CH:7]=[O:8])=[CH:5][CH:4]=[C:3]([CH:9]=[O:10])[CH:2]=1.[CH2:11]([Mg]Cl)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>O1CCCC1>[OH:8][CH:7]([C:6]1[CH:5]=[CH:4][C:3]([CH:9]=[O:10])=[CH:2][CH:1]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 12173TerephthalaldehydeHCID 178443579HCID 178443579, compound

Product 1

HCID 596917614-(1-Hydroxynon-1-yl)benzaldehydeYield 5.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Terephthaldicarboxaldehyde (2.00 g, 14.91 mmol) was dissolved in tetrahydrofuran (25 mL) and cooled to 0° C. Octylmagnesium chloride (7.5 mL, 2.0M in THF, 15 mmol) was added dropwise. After 15 min, the reaction was quenched with 2N aqueous hydrochloric acid (50 mL) and diluted with ethyl acetate (50 mL). The organic layer was separated, washed with sat'd sodium chloride (50 mL), dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography eluting with 9% ethyl acetate/hexane gave 0.19 g (0.77 mmol, 5.1%) of product: 1H NMR (500 MHz) δ 10.0 (s, 1H), 7.87 (d, J=8.0 Hz, 2H), 7.52 (d, J=8.3 Hz, 2H), 4.75-4.80 (m, 1H), 1.68-1.82 (m, 2H), 1.22-1.45 (m, 12H), 0.91 (t, J=7.0 Hz, 3H).

Workup

  1. customthe reaction was quenched with 2N aqueous hydrochloric acid (50 mL)
  2. additiondiluted with ethyl acetate (50 mL)
  3. customThe organic layer was separated
  4. washwashed with sat'd sodium chloride (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. washSilica gel chromatography eluting with 9% ethyl acetate/hexane

Sources & evidence

ORD record
ord-0914285cdb264f2785b263524a3066a3
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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