Methyl di-t-butyl hydroxyhydrocinnamate → HCID 20306448, compound

HRID 1732425Notes

Reaction equation

HRID 1732425 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2([CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([CH2:17][CH2:18][OH:19])[C:11]([CH3:21])([CH3:20])[CH2:10]2)[NH:6][C:5]1=[O:22].[C:23]([C:27]1[CH:28]=[C:29]([CH2:38][CH2:39][C:40](OC)=[O:41])[CH:30]=[C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:32]=1[OH:33])([CH3:26])([CH3:25])[CH3:24].[CH3:44][O-:45].[Na+]>C1(C)C(C)=CC=CC=1>[C:34]([C:31]1[CH:30]=[C:29]([CH2:38][CH2:39][C:40]([O:1][CH2:2][CH2:3][N:4]2[C:8](=[O:9])[C:7]3([CH2:14][C:13]([CH3:15])([CH3:16])[N:12]([CH2:17][CH2:18][O:19][C:40](=[O:41])[CH2:39][CH2:38][C:29]4[CH:28]=[C:27]([C:23]([CH3:25])([CH3:26])[CH3:24])[C:32]([OH:33])=[C:31]([C:34]([CH3:36])([CH3:37])[CH3:35])[CH:30]=4)[C:11]([CH3:21])([CH3:20])[CH2:10]3)[NH:6][C:5]2=[O:22])=[O:41])[CH:28]=[C:27]([C:23]([CH3:25])([CH3:24])[CH3:26])[C:44]=1[OH:45])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 62603Methyl di-t-butyl hydroxyhydrocinnamateHCID 10942334Sodium MethoxideHCID 20284703HCID 20284703, compound

Product 1

HCID 20306448HCID 20306448, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A mixture of 2.9 g of 3,8-bis(2-hydroxyethyl)-7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro [4.5]decane, 6.4 g of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and 0.3 g of sodium methoxide was refluxed for 8 hours in 300 ml of xylene, while removing 250 ml of xylene together with methanol formed in situ. After completion of the reaction, xylene was evaporated from the reaction under reduced pressure and the resulting residue was recrystallized from ligroin, giving the desired compound in the form of white crystals melting at 178°-179° C.

Workup

  1. customwhile removing 250 ml of xylene together with methanol
  2. customformed in situ
  3. customwas evaporated from the reaction under reduced pressure
  4. customthe resulting residue was recrystallized from ligroin

Sources & evidence

ORD record
ord-2aa229d54cf441b2bc95fae1df8fbc9e
Source dataset
uspto-grants-1980_12
Patent number
US04237294

Reaction notes

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