Formaldehyde → HCID 20343477, compound

HRID 2049727Notes

Reaction equation

HRID 2049727 reaction equation
[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:29])[CH:12]([CH2:27][CH3:28])[C:13]([O:15][CH:16]2[CH2:21][C:20]([CH3:23])([CH3:22])[N:19]([CH3:24])[C:18]([CH3:26])([CH3:25])[CH2:17]2)=[O:14])[CH2:4][C:3]1([CH3:31])[CH3:30].[CH3:32][N:33]1[C:38]([CH3:40])([CH3:39])[CH2:37][CH:36]([O:41][C:42](=[O:58])[CH2:43][C:44]([O:46][CH:47]2[CH2:52][C:51]([CH3:54])([CH3:53])[N:50]([CH3:55])[C:49]([CH3:57])([CH3:56])[CH2:48]2)=[O:45])[CH2:35][C:34]1([CH3:60])[CH3:59].[CH2:61]=O.[H-].[Na+].[C:65]([C:69]1[CH:70]=C([CH:76]=[C:77]([C:80]([CH3:83])([CH3:82])[CH3:81])[C:78]=1[OH:79])CN(C)C)([CH3:68])([CH3:67])[CH3:66].[C:84]1(C)C=CC=C[CH:85]=1>>[C:80]([C:77]1[CH:76]=[C:28]([CH2:27][C:12]([C:11]([O:10][CH:5]2[CH2:4][C:3]([CH3:30])([CH3:31])[N:2]([CH3:1])[C:7]([CH3:8])([CH3:9])[CH2:6]2)=[O:29])([C:13]([O:15][CH:16]2[CH2:21][C:20]([CH3:22])([CH3:23])[N:19]([CH3:24])[C:18]([CH3:26])([CH3:25])[CH2:17]2)=[O:14])[CH2:61][C:43]([C:42]([O:41][CH:36]2[CH2:35][C:34]([CH3:60])([CH3:59])[N:33]([CH3:32])[C:38]([CH3:39])([CH3:40])[CH2:37]2)=[O:58])([C:44]([O:46][CH:47]2[CH2:52][C:51]([CH3:54])([CH3:53])[N:50]([CH3:55])[C:49]([CH3:57])([CH3:56])[CH2:48]2)=[O:45])[CH2:84][CH3:85])[CH:70]=[C:69]([C:65]([CH3:68])([CH3:67])[CH3:66])[C:78]=1[OH:79])([CH3:83])([CH3:82])[CH3:81]

Participants

7

Reactant 6

HCID 712FormaldehydeHCID 1140TolueneHCID 24758Sodium hydrideHCID 66609Phenol, 4-[(dimethylamino)methyl]-2,6-bis(1,1-dimethylethyl)-HCID 20343467HCID 20343467, compoundHCID 20343478Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) propanedioate

Product 1

HCID 20343477HCID 20343477, compound

Procedure

21.9 g (0.05 mole) of ethylmalonic acid-bis-(1,2,2,6,6-pentamethyl-4-piperidinyl)ester, 20.5 g (0.05 mole) of malonic acid-bis-(1,2,2,6,6-pentamethyl-4-piperidinyl)ester, 1.5 g (0.05 mole) of paraformaldehyde and 0.5 g of NaH are stirred in 120 ml of toluene for half an hour at room temperature and then for 7 hours at reflux temperature. After cooling, there is added 13.2 g (0.05 mole) of N-(3,5-di-tert.butyl-4-hydroxybenzyl)-dimethylamine, and the mixture is heated for 4 hours under reflux. Processing analogously to Example 1 yields 1-(3,5-di-tert.butyl-4-hydroxyphenyl)-2,2,4,4-tetra-(1,2,2,6,6-pentamethyl-4-piperidinyloxycarbonyl)-hexane as an oily residue.

Workup

  1. temperaturefor 7 hours at reflux temperature
  2. temperatureAfter cooling
  3. temperaturethe mixture is heated for 4 hours
  4. temperatureunder reflux

Sources & evidence

ORD record
ord-79536e3b95fb44b097ab290b107767e1
Source dataset
uspto-grants-1980_04
Patent number
US04198334

Reaction notes

Loading…