Pyridine → 8-Acetoxy-2,6-dimethyl-5-hydroxy-2-octene

HRID 1447534Notes

Reaction equation

HRID 1447534 reaction equation
[CH3:1][CH:2]([CH:6]([OH:12])[CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH2:3][CH2:4][OH:5].[C:13](OC(=O)C)(=[O:15])[CH3:14].N1C=CC=CC=1>CCOCC>[C:13]([O:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH:6]([OH:12])[CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 136688813,7-Dimethyl-4-hydroxy-6-octen-1-ol

Product 1

HCID 233414518-Acetoxy-2,6-dimethyl-5-hydroxy-2-octeneYield 45%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 3,7-dimethyl-4-hydroxy-6-octen-1-ol (5.06 g, 29 mmole), acetic anhydride (3.06 g, 30 mmole), pyridine (4.75 g, 60 mmole) and ether (100 ml) is stirred at room temperature for 16 hours. The resulting mixture is treated with ether (200 ml) and washed with saturated cupric sulfate solution (2×100 ml). The organic phase is dried (Na2SO4) and evaporated in vacuo to give 8-acetoxy-2,6-dimethyl-5-hydroxy-2-octene as a colorless oil (2.27 g, 45%).

Workup

  1. washwashed with saturated cupric sulfate solution (2×100 ml)
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-1353d9ec759d4c5dba298b2e8292cec1
Source dataset
uspto-grants-1979_12
Patent number
US04177194

Reaction notes

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