4-nonylbenzoyl Chloride → 4-Nonylbenzaldehyde

HRID 1454324Notes

Reaction equation

HRID 1454324 reaction equation
[CH2:1]([C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C1COCC1>[CH2:1]([C:10]1[CH:11]=[CH:12][C:13]([CH:14]=[O:15])=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 27534144-nonylbenzoyl ChlorideHCID 16710494Lithium tri-tert-butoxyaluminohydride

Product 1

HCID 109333644-NonylbenzaldehydeYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.0 g (7.5 mmol) of 4-nonylbenzoyl chloride in 75 mL of THF at −78° C. was treated with 7.5 mL (7.5 mmol) of 1M lithium tri-(tert-butoxy) aluminum hydride in THF. After 30 min at −78° C., the reaction was quenched with 2N HCl and was allowed to warm to rt. The mixture was poured into Et2O and washed with 2N HCl, sat'd NaHCO3 and sat'd NaCl. The organic layer was dried over MgSO4 and concentrated. The residue was purified on a 40M Biotage column using 100:1 v/v hexane/Et2O as the eluant to afford 708 mg (41%) of the title compound: 1H-NMR (500 MHz) δ 0.87 (t, J=7.0, 3H), 1.26-1.31 (m, 12H), 1.60-1.66 (m, 2H), 2.68 (t, J=7.8, 2H), 7.32 (d, J=8.0, 2H), 7.79 (d, J=8.0, 2H), 9.97 (s, 1H).

Workup

  1. customthe reaction was quenched with 2N HCl
  2. additionThe mixture was poured into Et2O
  3. washwashed with 2N HCl
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on a 40M Biotage column

Sources & evidence

ORD record
ord-d196bfc0ce7a40fc9a0ce1597c05cb9e
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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