Ammonium Chloride → (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-penten-1-ol

HRID 1195476Notes

Reaction equation

HRID 1195476 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15]/[C:16](/[CH3:22])=[CH:17]\[C:18](OC)=[O:19].COCCO[AlH2-]OCCOC.[Na+].[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15]/[C:16](/[CH3:22])=[CH:17]\[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 16684438Red-AlHCID 88611456methyl (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate

Product 1

HCID 22843765(Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-penten-1-olYield 53.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 0.8 g (2.6 mmol) of methyl (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate in toluene (5 ml) was treated dropwise with 0.75 ml of a 3.5 molar Red-Al solution in toluene. After 2 hours at room temperature the mixture was poured into saturated ammonium chloride solution and extracted with ether. The combined extracts were washed with water, dried and concentrated to a colourless oil which was purified on silica gel with hexane/ethyl acetate 9:1→6:1, yielding 0.39 g of crystalline (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-penten-1-ol. M.P. 58.5°-60° C.

Workup

  1. extractionextracted with ether
  2. washThe combined extracts were washed with water
  3. customdried
  4. concentrationconcentrated to a colourless oil which
  5. customwas purified on silica gel with hexane/ethyl acetate 9:1→6:1

Sources & evidence

ORD record
ord-cf44356218ad4156981b0e94c23c8bde
Source dataset
uspto-grants-1992_05
Patent number
US05110955

Reaction notes

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