Propanal → HCID 14692984, compound

HRID 1608069Notes

Reaction equation

HRID 1608069 reaction equation
[Cl-].C[Al+]C.CCCCCC.[CH3:11][C:12]1[CH2:17][C:16]([CH3:19])([CH3:18])[CH:15]([C:20]([CH3:22])=[CH2:21])[C:14]([CH3:24])([CH3:23])[CH:13]=1.[CH:25](=[O:28])[CH2:26][CH3:27]>ClCCl>[CH2:26]([CH:25]([OH:28])[CH2:21][C:20](=[CH2:22])[CH:15]1[C:16]([CH3:18])([CH3:19])[CH2:17][C:12]([CH3:11])=[CH:13][C:14]1([CH3:24])[CH3:23])[CH3:27]

Participants

6

Reactant 4

HCID 527PropanalHCID 8058HexaneHCID 1731563,3,5,5-TetramethyllimoneneHCID 16686359Dimethylalumanylium chloride

Product 1

HCID 14692984HCID 14692984, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Dimethylaluminum chloride (60 mL of a 1M hexane solution) was added dropwise to a solution of 1,3,3,5,5-pentamethyl-4-(1-methylethenyl)-1-cyclohexene (7.70 g, 0.04 mol) and propionaldehyde (2.30 g, 0.04 mol) in dichloromethane (150 mL) at 25°-30° C. over a 15 min period. The mixture was stirred at 25° C. for 16 h. Work-up (as described in Example 2) and chromatography provided 2.20 g of α-ethyl-2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol, bp (kugelrohr bath) 125° C., 0.5 mm, (GLC purity, two isomers, 40.7% and 57.9%). 1H-NMR (60 MHz, CDCl3) δ0.98 and 1.03 (12H, 2s), 1.02 (3H, t, J=4 Hz), 1.63 (3H, s), 1.1-2.6 (8H, m), 3.5-3.9 (1H, m), 5.0-5.3 (3 H, broad s); IR (film) vmax 3350, 2950, 1640, 1460, 1380, 1360 cm-1 ; MS m/e 250, 235, 217, 125, 107, 96. The mass spectra of the diastereomers were nearly identical.

Sources & evidence

ORD record
ord-c41ed261b834434e99faf091bcb6b1be
Source dataset
uspto-grants-1989_09
Patent number
US04868339

Reaction notes

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