HCID 14457497, compound → HCID 69963640, compound

HRID 1458287Notes

Reaction equation

HRID 1458287 reaction equation
[Al].[Li].[CH2:3]([O:13][C:14]1[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][CH:15]=1)/[CH:4]=[C:5](/[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])\[CH3:6]>O>[CH2:3]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][OH:19])=[CH:22][CH:23]=1)/[CH:4]=[C:5](/[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])\[CH3:6]

Participants

4

Reactant 2

HCID 14457497HCID 14457497, compoundHCID 16211445Aluminum;lithium

Product 1

HCID 69963640HCID 69963640, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of lithium aluminum hydridete (7.59 g) in trahydrofuran (200 ml) was added a solution of the raw product of methyl 4-geranyloxybenzoate in tetrahydrofuran anhydride (100 ml) dropwise while being cooled with ice. After being stirred for 1 hour at room temperature, the reaction solution, with water (200 ml) added thereto, was extracted with ethyl acetate (400 ml). The extract was dried over sodium sulfite anhydride and then the solvent was evaporated under a vacuum. The residue was recrystallized from an n-hexane/ethyl acetate mixed solution, thereby yielding 34.4 g (66%) of the aimed compound.

Workup

  1. temperaturewhile being cooled with ice
  2. extractionwas extracted with ethyl acetate (400 ml)
  3. dry with materialThe extract was dried over sodium sulfite anhydride
  4. customthe solvent was evaporated under a vacuum
  5. customThe residue was recrystallized from an n-hexane/ethyl acetate mixed solution

Sources & evidence

ORD record
ord-4ace4db1dcd441498f9804d252bf413c
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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