Ammonium Chloride → HCID 54544629, compound

HRID 846620Notes

Reaction equation

HRID 846620 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[CH:5]=[CH:6][C:7](OCC)=[O:8].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[CH:5]=[CH:6][CH2:7][OH:8]

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 53893451HCID 53893451, compound

Product 1

HCID 54544629HCID 54544629, compoundYield 54%

Procedure

To a tetrahydrohydrofuran solution containing 27.5 g of ethyl 3-methyl-p-(2-tetrahydropyranyloxy)cinnamate was added dropwise 118 ml of diisobutyl aluminium hydride (25% by weight/volume) at a room temperature. After 2 hours, the reaction mixture was poured into an ice-cooled ammonium chloride aqueous solution, and the insoluble matters were removed by filtration. The filtrate was washed with water then dried with anhydrous sodium sulfate and concentrated. The residue thus obtained was purified by means of silica gel column chromatography to yield 12.7 g of 3-methyl-p-(2-tetrahydropyranyloxy)cinnamyl alcohol in the form of colorless oily substance.

Workup

  1. customthe insoluble matters were removed by filtration
  2. washThe filtrate was washed with water
  3. dry with materialthen dried with anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue thus obtained
  6. customwas purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-d41155875df744c1be2fb2f974c320c5
Source dataset
uspto-grants-1992_08
Patent number
US05137889

Reaction notes

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