Sodium Methoxide → Rhodoxanthin

HRID 267318Notes

Reaction equation

HRID 267318 reaction equation
[CH3:1][C:2](=[CH:7][CH:8]=[CH:9][C:10]([CH3:23])=[CH:11][CH:12]=[C:13]1[C:18]([CH3:20])([CH3:19])[CH2:17][C:16](=[O:21])[CH:15]=[C:14]1[CH3:22])[CH:3]=[CH:4][CH:5]=O.[Br-].C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:44][C:45](=[CH:47][CH:48]=[CH:49][C:50]([CH3:63])=[CH:51][CH:52]=[C:53]1[C:58]([CH3:60])([CH3:59])[CH2:57][C:56](=[O:61])[CH:55]=[C:54]1[CH3:62])[CH3:46].C[O-].[Na+]>CO>[CH3:62][C:54]1=[CH:55][C:56]([CH2:57][C:58]([CH3:60])([CH3:59])/[C:53]/1=[CH:52]\[CH:51]=[C:50](/[CH3:63])\[CH:49]=[CH:48]\[CH:47]=[C:45](/[CH3:44])\[CH:46]=[CH:5]\[CH:4]=[CH:3]\[C:2](\[CH3:1])=[CH:7]\[CH:8]=[CH:9]\[C:10](\[CH3:23])=[CH:11]\[CH:12]=[C:13]1/[C:18]([CH3:20])([CH3:19])[CH2:17][C:16]([CH:15]=[C:14]/1[CH3:22])=[O:21])=[O:61]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 54082787HCID 54082787, compoundHCID 88838348HCID 88838348, compound

Product 1

HCID 5281251Rhodoxanthin

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.2 g. of 4,8-dimethyl-10-(4-oxo-2,6,6-trimethyl-2-cyclohexenylidene)-2,4,6,8-decatetraenal and 0.35 g. of 2,6-dimethyl-8-(4-oxo-2,6,6-trimethyl-2-cyclohexenylidene)-2,4,6-octatrien triphenylphosphonium bromide were dissolved in 6 ml. of methanol and treated with 0.2 g. of sodium methoxide at 0° for 4 hours. The precipitated dark violet solid was collected and recrystallized from benzene methanol to yield rhodoxanthin.

Workup

  1. customThe precipitated dark violet solid was collected
  2. customrecrystallized from benzene methanol

Sources & evidence

ORD record
ord-48a3247cf06c4d7584ce5d7a59f248ee
Source dataset
uspto-grants-1976_03
Patent number
US03941841

Reaction notes

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