Ammonium Chloride → 1-(Benzyloxy)pent-4-en-2-ol

HRID 1290347Notes

Reaction equation

HRID 1290347 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:12]([Mg]Br)[CH:13]=[CH2:14].[Cl-].[NH4+]>C(OCC)C>[C:1]1([CH2:7][O:8][CH2:9][CH:10]([OH:11])[CH2:14][CH:13]=[CH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 108989(Phenylmethoxy)acetaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 100354781-(Benzyloxy)pent-4-en-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring 0° C. solution of 59.0 g of product from Example 1 in 375 ml of diethyl ether is added, dropwise, 432.24 ml of 1M allylmagnesium bromide in ether. The reaction is stirred at 0° C. for 1 hour, followed by overnight stirring at room temperature. The reaction is cooled to 0° C., hydrolyzed with saturated ammonium chloride, and the layers are separated. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo to give the product as an oil. The crude oil is purified by Kugelrohr distillation (bath temperature 100° C.) to give 61.5 g of the desired product as a colorless oil.

Workup

  1. waitfollowed by overnight
  2. stirringstirring at room temperature
  3. customthe layers are separated
  4. washThe organic layer is washed with saturated sodium chloride
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e0b911c007c4038b4f6899a13507d8f
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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