Hydrochloric Acid → (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

HRID 48547

Reaction equation

HRID 48547 reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH2:4][OH:5].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].BrC1C=CC=CC=1C=O.Cl>C1CCCCC1.CCCCCC>[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH:4]=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11143Aluminum isopropoxideHCID 811292-BromobenzaldehydeHCID 445070Farnesol

Product 1

HCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienalYield 96%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol (266 mg, 1.2 mmol) was dissolved in cyclohexane (1 mL), added with aluminum isopropoxide (24.5 mg, 0.1 eq, 0.12 mmol) and 2-bromobenzaldehyde (289 mg, 1.3 eq, 1.56 mmol) and stirred at room temperature for 1.5 hours. The reaction mixture was added with hexane, then made acidic with addition of 1 N hydrochloric acid and extracted twice with ethyl acetate. Subsequently, the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain 256 mg (yield: 96%, E:Z=99:1) of the title compound as yellow oil.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washSubsequently, the organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-8d2b06e5645d456589650ccc5af6f5cb
Source dataset
uspto-grants-2004_03
Patent number
US06703527B2

Linked notes

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