4'-Hydroxyacetophenone → HCID 54110922, compound

HRID 1284211Notes

Reaction equation

HRID 1284211 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.Cl[CH2:14][CH:15]=[CH:16][CH2:17][CH2:18][O:19][CH:20]([CH3:22])[CH3:21]>COCCOC>[CH:20]([O:19][CH2:18][CH2:17][CH:16]=[CH:15][CH2:14][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 14797Potassium HydroxideHCID 54043382HCID 54043382, compound

Product 1

HCID 54110922HCID 54110922, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

3.4 g (0.06 mol) of pulverised potassium hydroxide are added to a solution of 8.2 g (0.06 mol) of p-hydroxy-acetophenone and 14.6 g (0.09 mol) of 1-chloro-5-isopropoxy-2-pentene in 100 cc of 1,2-dimethoxyethane. The mixture is stirred at 60° during the course of 24 hours and is subsequently filtered. The filtrate is evaporated at reduced pressure, the residue is taken up in ether, and the ether solution is washed with saturated salt solution. The organic phase is dried with sodium sulphate and evaporated. The residue is chromatographed with hexane/ethyl acetate 4 : 1 on silica gel and then the 4'-(5-isopropoxy-2-pentenyloxy)-acetophenone is obtained as colourless oil. nD20 = 1.5240.

Workup

  1. filtrationis subsequently filtered
  2. customThe filtrate is evaporated at reduced pressure
  3. washthe ether solution is washed with saturated salt solution
  4. dry with materialThe organic phase is dried with sodium sulphate
  5. customevaporated
  6. customThe residue is chromatographed with hexane/ethyl acetate 4 : 1 on silica gel

Sources & evidence

ORD record
ord-494a535c40f24555a8231ef2c299450c
Source dataset
uspto-grants-1976_08
Patent number
US03978134

Reaction notes

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