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

HRID 48547

反応式

HRID 48547 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 8078Cyclohexane溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-8d2b06e5645d456589650ccc5af6f5cb
出典データセット
uspto-grants-2004_03
特許番号
US06703527B2

関連ノート

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