Ammonium Chloride → HCID 54544629, compound

HRID 2291351Notes

Reaction equation

HRID 2291351 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. 2 Hours after the dropwise addition, the reaction mixture was poured into an ice-cooled ammonium chloride aqueous solutoin, 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. addition2 Hours after the dropwise addition
  2. customthe insoluble matters were removed by filtration
  3. washThe filtrate was washed with water
  4. dry with materialthen dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-05586cca3270405393d8cbcd3a296147
Source dataset
uspto-grants-1989_01
Patent number
US04795814

Reaction notes

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