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

HRID 27650Notes

Reaction equation

HRID 27650 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-450b26c577d74c318313e8d213671319
Source dataset
uspto-grants-1980_09
Patent number
US04222937

Reaction notes

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