Ethyl vinyl ether → 8-Acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene

HRID 1447535Notes

Reaction equation

HRID 1447535 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]([CH3:15])[CH:8]([OH:14])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])(=[O:3])[CH3:2].[CH2:16]([O:18][CH:19]=[CH2:20])[CH3:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[C:1]([O:4][CH2:5][CH2:6][CH:7]([CH3:15])[CH:8]([O:14][CH:16]([O:18][CH2:19][CH3:20])[CH3:17])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 521998p-Toluenesulfonic acid monohydrateHCID 233414518-Acetoxy-2,6-dimethyl-5-hydroxy-2-octene

Product 1

HCID 233414488-Acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 8-acetoxy-2,6-dimethyl-5-hydroxy-2-octene (2.27 g, 10.6 mmole), ethyl vinylether (0.82 g. 11.4 mmole), p-toluenesulfonic acid monohydrate (catalytic amount) and ether (50 ml) is stirred at room temperature for 16 hours. The resulting mixture is treated with ether (150 ml) and washed with 5% sodium bicarbonate solution (2×100 ml). The organic phase is dried (Na2SO4), and evaporated in vacuo to give the crude product. The crude material is further purified by column chromatography on silica gel (25 g, 5% ethyl acetate in hexane) to give 8-acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene as a colorless oil.

Workup

  1. washwashed with 5% sodium bicarbonate solution (2×100 ml)
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give the crude product
  5. customThe crude material is further purified by column chromatography on silica gel (25 g, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-31a9d5415a9745a69b4b5b996cf65769
Source dataset
uspto-grants-1979_12
Patent number
US04177194

Reaction notes

Loading…