Hydrochloric Acid → HCID 22979405, compound

HRID 1861582Notes

Reaction equation

[OH:1][C:2]1[C:9]([O:10][CH2:11][C@@H:12]([CH3:15])[CH2:13][CH3:14])=[C:8]([O:16][CH2:17][C@@H:18]([CH3:21])[CH2:19][CH3:20])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[CH3:15][C@@H:12]([CH2:13][CH3:14])[CH2:11][O:10][C:9]1[C:2]([O:1][CH2:27][CH2:26][CH2:25][CH:24]=[CH2:23])=[C:3]([CH:6]=[CH:7][C:8]=1[O:16][CH2:17][C@@H:18]([CH3:21])[CH2:19][CH3:20])[CH:4]=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

Under nitrogen atmosphere, a mixture of 2-hydroxy-3,4-bis-[(S)-2-methyl-butoxy]-benzaldehyde (0.74 9, 2.51 mmol), 5-bromo-1-pentene (0.45 g, 3.02 mmol) and potassium carbonate (0.41 g, 3 mmol) in dry DMF (5 ml) was stirred at 80° C. for 3 h. The cooled reaction mixture was gently poured into HCl 3N (15 ml) and extracted with diethylether (3×20 ml). The combined organic extracts are washed with 30 ml of saturated NaCl solution, dried over magnesium sulphate and evaporated under reduced pressure. The obtained oily residue was chromatographed on silica (diethylether/petroleumether: 1/3) to give 3,4-bis-[(S)-2-methyl-butoxy]-2-(pent-4-enyloxy)-benzaldehyde as a slightly yellow oil (Yield: 0.82 g, 90%).

Workup

customThe cooled reaction mixture
extractionextracted with diethylether (3×20 ml)
washThe combined organic extracts are washed with 30 ml of saturated NaCl solution
dry with materialdried over magnesium sulphate
customevaporated under reduced pressure
customThe obtained oily residue was chromatographed on silica (diethylether/petroleumether: 1/3)

Sources & evidence

ORD record: ord-5191c2bde2f94a279f76caa93350326b
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06534135B1

Reaction notes

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