Benzaldehyde → HCID 131726545, compound

HRID 852869Notes

Reaction equation

HRID 852869 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br-].[C:12]([CH:15](C)[CH2:16][CH2:17][CH2:18][CH2:19][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:14])=[O:13]>C1COCC1>[C:2]1(/[CH:1]=[CH:19]\[CH2:18][CH2:17][CH2:16][CH2:15][C:12]([OH:14])=[O:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24758Sodium hydrideHCID 85805963HCID 85805963, compound

Product 1

HCID 131726545HCID 131726545, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Benzaldehyde (6.63 g, 0.062 mol, 6.35 ml) in dry THF (20 ml) was added dropwise to a stirred suspension of NaH (60% dispersion, 5.51 g, 0.138 mol) and (5-carboxyhexyl)-triphenylphosphonium bromide (30 g, 0.066 mol) in dry THF (260 ml). After stirring overnight, the solvent was evaporated to dryness, and the residue taken up into water (300 ml). The solution was made alkaline (pH 12-14) with NaOH solution (4 M) and extracted with EtOAc. The basic solution was then acidified (conc. HCl), extracted with Et2O, and the combined extracts washed with brine and dried with MgSO4. Removal of the solvent afforded 16.5 g of crude product which was purified by chromatography (silica, 1:5 EtOAc/petroleum ether, increasing to 1:1 EtOAc/petroleum ether toward completion) to give 10.81 g (85%) of E-/Z-7-phenylhept-6-ene-oic acid (˜1:1 mixture) as a pale yellow oil. Hydrogenation of the unsaturated acid (10% Pd—C, EtOAc) afforded the saturated compound (51): 1H NMR (CDCl3) δ 11.57 (br s, 1H), 7.20 (m, 5H), 2.58 (t, J=7.7 Hz, 2H), 2.31 (t, J=7.5 Hz, 2H), 1.61 (m, 4H), 1.33 (m, 4H). 13C NMR (CDCl3), δ 180.8, 142.7, 128.5, 128.4, 125.7, 36.0, 34.2, 31.4, 29.0, 24.7.

Workup

  1. customthe solvent was evaporated to dryness
  2. extractionextracted with EtOAc
  3. extractionextracted with Et2O
  4. washthe combined extracts washed with brine
  5. dry with materialdried with MgSO4
  6. customRemoval of the solvent
  7. customafforded 16.5 g of crude product which
  8. customwas purified by chromatography (silica, 1:5 EtOAc/petroleum ether, increasing to 1:1 EtOAc/petroleum ether toward completion)

Sources & evidence

ORD record
ord-9ffde659660948a69ec5c7efd8bc3bd5
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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