Benzyl Alcohol → HCID 11735856, compound

HRID 1079027Notes

Reaction equation

HRID 1079027 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:15][CH:16]([CH2:20][CH:21]=[CH2:22])[C:17](Cl)=[O:18]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:2]1([CH2:1][O:8][C:17](=[O:18])[CH:16]([CH3:15])[CH2:20][CH:21]=[CH2:22])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 129214422-Methyl-4-pentenoyl chloride

Product 1

HCID 11735856HCID 11735856, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 23.8 g of benzyl alcohol, 0.05 g of 4-(dimethylamino)pyridine, 18.3 g of pyridine and 250 ml of methylene chloride is added, dropwise, a solution of 29.5 g of racemic 2-methyl-4-pentenoyl chloride in 50 ml of methylene chloride. The mixture is stirred at room temperature for 4 hours, followed by successive washing with 2N hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride. The organic layer is dried and concentrated in vacuo. The residue is purified by Kugelrohr distillation to give 35.2 g of the desired product as a colorless oil; bp 70°-75° C. at 0.10 mm Hg.

Workup

  1. washby successive washing with 2N hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride
  2. customThe organic layer is dried
  3. concentrationconcentrated in vacuo
  4. distillationThe residue is purified by Kugelrohr distillation

Sources & evidence

ORD record
ord-e2926d776f9d4c0f95dfbf159ab02af4
Source dataset
uspto-grants-1996_08
Patent number
US05550257

Reaction notes

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