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

HRID 54763Notes

Reaction equation

HRID 54763 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-8d08157a102b4f9c89a6a53c15e800da
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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