Acetic Acid → HCID 20449623, compound

HRID 358232Notes

Reaction equation

HRID 358232 reaction equation
[CH3:1][C:2]1([CH3:39])[CH2:7][CH:6]([O:8][C:9](=[O:36])[CH2:10][CH:11]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([OH:31])=[C:26]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:25]=2)[C:12]2[C:17]([CH3:18])=[CH:16][C:15]([OH:19])=[C:14]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:13]=2)[CH2:5][C:4]([CH3:38])([CH3:37])[NH:3]1.[C:40](O)(=[O:42])[CH3:41]>C(OC(=O)C)(=O)C>[C:40]([N:3]1[C:2]([CH3:39])([CH3:1])[CH2:7][CH:6]([O:8][C:9](=[O:36])[CH2:10][CH:11]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([OH:31])=[C:26]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:25]=2)[C:12]2[C:17]([CH3:18])=[CH:16][C:15]([OH:19])=[C:14]([C:20]([CH3:21])([CH3:22])[CH3:23])[CH:13]=2)[CH2:5][C:4]1([CH3:38])[CH3:37])(=[O:42])[CH3:41]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 20449621HCID 20449621, compound

Product 1

HCID 20449623HCID 20449623, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

10 g of 2,2,6,6-tetramethyl-4-[3,3-bis-(3-tert.-butyl-6-methyl-4-hydroxyphenyl)-propionyloxy]-piperidine are stirred in 25 ml of acetic anhydride at 110° for 6 hours. The acetic acid formed and excess anhydride are then distilled off under vacuum as completely as possible. The residue is cooled down to room temperature, 100 ml of water are added and are mixed in efficiently, and the precipitate is filtered off, is washed with water and is dried. Crystallising from acetonitrile gives 1-acetyl-2,2,6,6-tetramethyl-4-[3,3-bis-(3-tert.-butyl-6-methyl-4-hydroxyphenyl)-propionyloxy]-piperidine having a melting point of 270° (optical stabiliser No. 2).

Workup

  1. distillationexcess anhydride are then distilled off under vacuum as completely as possible
  2. addition100 ml of water are added
  3. additionare mixed in efficiently, and the precipitate
  4. filtrationis filtered off
  5. washis washed with water
  6. customis dried
  7. customCrystallising from acetonitrile

Sources & evidence

ORD record
ord-745eeec8f5b3411995450ca670e9917f
Source dataset
uspto-grants-1984_08
Patent number
US04465765

Reaction notes

Loading…