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

HRID 1454334Notes

Reaction equation

HRID 1454334 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 minutes, 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 NaCl (50 ml), dried over magnesium sulfate and concentrated. Silica gel chromatography eluting with 91:9 v/v hexane/EtOAc gave 0.19 g (0.77 mmol, 5.1%) of the title compound: 1H NMR (500 MHz) δ 10.0 (s, 1H), 7.87 (d, J=8.0, 2H), 7.52 (d, J=8.3, 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, 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 NaCl (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washSilica gel chromatography eluting with 91:9 v/v hexane/EtOAc

Sources & evidence

ORD record
ord-f4428c4574d3426c92493e469070e0a9
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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