1-Butanol → Butyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoate

HRID 460960Notes

Reaction equation

HRID 460960 reaction equation
[CH2:1]([O:5][C:6](=[O:12])/[CH:7]=[C:8](\[CH:10]=O)/[CH3:9])[CH2:2][CH2:3][CH3:4].[CH2:13]([OH:17])[CH2:14][CH2:15][CH3:16].[CH2:18](N(CC)CC)C>O>[CH2:1]([O:5][C:6](=[O:12])[CH:7]=[C:8]([CH3:9])[CH:10]=[CH:16][CH:15]=[C:14]([CH:13]=[O:17])[CH3:18])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-Butanol2×HCID 8471TriethylamineHCID 867352413-Formyl-crotonic acid butyl ester

Product 1

HCID 53845956Butyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

212.6 G. of 2-formyl-but-2-ene-4-triphenyl-phosphonium chloride and 95 g. of 3-formyl-crotonic acid butyl ester are introduced into 1100 ml. of butanol and treated at 5° C. with a solution of 57 g. of triethylamine in 60 ml. of butanol. The reaction mixture is subsequently stirred for 6 hours at 25° C., then cooled and introduced into water and thoroughly extracted with hexane. The hexane phase is washed first repeatedly with methanol/water (6:4 parts by volume), then with water, dried over sodium sulphate and filtered. The filtrate is isomerized for 12 hours by shaking with iodine. The iodine is removed by the addition of sodium thiosulphate. The filtrate is washed again with water, dried and evaporated under reduced pressure. The remaining 7-formyl-3-methyl-octa-2,4,6-trien-1-oic acid butyl ester boils, after rectification, at 102°-105° C/0.09 mm Hg.

Workup

  1. temperaturecooled
  2. extractionthoroughly extracted with hexane
  3. washThe hexane phase is washed first repeatedly with methanol/water (6:4 parts by volume)
  4. dry with materialwith water, dried over sodium sulphate
  5. filtrationfiltered
  6. waitThe filtrate is isomerized for 12 hours
  7. stirringby shaking with iodine
  8. customThe iodine is removed by the addition of sodium thiosulphate
  9. washThe filtrate is washed again with water
  10. customdried
  11. customevaporated under reduced pressure
  12. customat 102°-105° C

Sources & evidence

ORD record
ord-0fd09b9441fc4c95907e686359a1b602
Source dataset
uspto-grants-1977_12
Patent number
US04061656

Reaction notes

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