HCID 13235817, compound → 4-(4-Chlorophenyl)pent-4-en-1-ol

HRID 462878Notes

Reaction equation

HRID 462878 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:15])[CH2:9][CH2:10][C:11](OC)=[O:12])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[CH2:15])[CH2:9][CH2:10][CH2:11][OH:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13235817HCID 13235817, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 132358184-(4-Chlorophenyl)pent-4-en-1-olYield 93.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of methyl 4-(4-chlorophenyl)pent-4-enoate (5.5 g) in dry diethyl ether (20 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.9 g) in dry diethyl ether (130 ml), cooled in an ice-water bath and under an atmosphere of nitrogen. Following the addition, the cooling bath was removed and the reaction mixture was stirred for 1 hour at room temperature and then diluted with aqueous ammonium chloride. The mixture was extracted with diethyl ether, and the extracts were washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give 4-(4-chlorophenyl)pent-4-en-1-ol (4.5 g, 93%) as a pale yellow oil, IR (film): 3400 cm-1.

Workup

  1. temperaturecooled in an ice-water bath and under an atmosphere of nitrogen
  2. additionthe addition
  3. customthe cooling bath was removed
  4. additiondiluted with aqueous ammonium chloride
  5. extractionThe mixture was extracted with diethyl ether
  6. washthe extracts were washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-675780d8e41b44a388cee25a033ac2bf
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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