Sodium ethoxide → HCID 53847767, compound

HRID 972967Notes

Reaction equation

HRID 972967 reaction equation
[Cl-].[Cl:2][C:3]1[C:28]([CH3:29])=[C:27]([O:30][CH3:31])[C:26]([CH3:32])=[C:25]([CH3:33])[C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:34]([O:36][C:37](=[O:48])[CH:38]=[C:39]([CH3:47])[CH:40]=[CH:41][CH:42]=[C:43]([CH:45]=O)[CH3:44])[CH3:35].CC[O-].[Na+].[Na]>C(O)C.CN(C)C=O>[CH2:34]([O:36][C:37](=[O:48])[CH:38]=[C:39]([CH3:47])[CH:40]=[CH:41][CH:42]=[C:43]([CH3:45])[CH:44]=[CH:5][C:4]1[C:25]([CH3:33])=[C:26]([CH3:32])[C:27]([O:30][CH3:31])=[C:28]([CH3:29])[C:3]=1[Cl:2])[CH3:35]

Participants

7

Reactant 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 54295620Ethyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoateHCID 86735148HCID 86735148, compound

Product 1

HCID 53847767HCID 53847767, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

9.9 g. of 2-chloro-4-methoxy-3,5,6-trimethyl-benzyl-triphenylphosphonium chloride are dissolved in 50 ml. of dimethylformamide. After the addition of 4.16 g. of 7-formyl-3-methyl-octa-2,4,6-trien-1-oic acid ethyl ester, the solution is treated dropwise at 20° C. with 10 ml. of a solution of sodium ethylate freshly prepared from 0.460 g. of sodium and 10 ml. of absolute ethanol. The mixture is stirred at room temperature for 12 hours, then introduced into 100 ml. of water and extracted with hexane. The hexane extract is shaken out three times with methanol/water, dried over sodium sulphate and evaporated under reduced pressure. The residue is purified by absorption on silica gel using methylene chloride/hexane (8:2 parts by volume) for the elution. The 9-(2-chloro-4-methoxy-3,5,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester obtained from the eluate melts at 90° C. after recrystallisation from hexane.

Workup

  1. additionAfter the addition of 4.16 g
  2. additionintroduced into 100 ml
  3. extractionof water and extracted with hexane
  4. extractionThe hexane extract
  5. stirringis shaken out three times with methanol/water
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customThe residue is purified by absorption on silica gel
  9. washfor the elution

Sources & evidence

ORD record
ord-27fb9462f1ab45b9a26277da5f5380f3
Source dataset
uspto-grants-1977_10
Patent number
US04054589

Reaction notes

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