Methyl di-t-butyl hydroxyhydrocinnamate → 3,9-Bis[2-{3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane

HRID 1761977Notes

Reaction equation

HRID 1761977 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[OH:22][CH2:23][C:24]([CH:27]1[O:32][CH2:31][C:30]2([CH2:37][O:36][CH:35]([C:38]([CH3:42])([CH3:41])CO)[O:34][CH2:33]2)[CH2:29][O:28]1)([CH3:26])[CH3:25].[CH3:43][O-:44].[Na+]>>[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([O:20][CH2:21][C:38]([CH:35]2[O:34][CH2:33][C:30]3([CH2:29][O:28][CH:27]([C:24]([CH3:26])([CH3:25])[CH2:23][O:22][C:18](=[O:19])[CH2:17][CH2:16][C:7]4[CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:43]([OH:44])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=4)[O:32][CH2:31]3)[CH2:37][O:36]2)([CH3:42])[CH3:41])=[O:19])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 62603Methyl di-t-butyl hydroxyhydrocinnamateHCID 7569008beta3,beta3,beta9,beta9-Tetramethyl-2,4,8,10-tetraoxaspiro(5.5)undecane-3,9-diethanolHCID 10942334Sodium Methoxide

Product 1

HCID 166630863,9-Bis[2-{3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecaneYield 169.7%

Procedure

A mixture of 35.3 g (0.121 mole) of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 15.3 g (0.0503 mole) of 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane and 0.82 g (0.015 mole) of sodium methoxide was reacted, after-treated and purified in the same manner as in Preparation example 1, to obtain 21 g of white crystalline 3,9-bis{2-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxy]-1,1-dimethylethyl}-2,4,8,10-tetraoxaspiro[5.5]-undecane having a purity of 99% (compound AO-1). m.p., 98°-100° C.

Workup

  1. customwas reacted
  2. additionafter-treated
  3. custompurified in the same manner as in Preparation example 1

Sources & evidence

ORD record
ord-686f046f79484d16bc412f369479e759
Source dataset
uspto-grants-1989_05
Patent number
US04829112

Reaction notes

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