Acetic Acid → Alpha-Tocopherol Acetate

HRID 2396935Notes

Reaction equation

HRID 2396935 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[C:7]([CH3:13])[C:6]=1[CH3:14])(=[O:3])[CH3:2].[CH3:15][C:16]([CH2:18][CH2:19][CH2:20][CH:21]([CH3:33])[CH2:22][CH2:23][CH2:24][CH:25]([CH3:32])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[CH2:17].C=O.[CH2:36](NCCCC)CCC.C(O)(=O)C>>[CH3:36][C:9]1[C:10]([CH3:11])=[C:5]([O:4][C:1]([CH3:2])=[O:3])[C:6]([CH3:14])=[C:7]2[CH2:13][CH2:17][C@:16]([CH2:18][CH2:19][CH2:20][C@@H:21]([CH2:22][CH2:23][CH2:24][C@@H:25]([CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH3:32])[CH3:33])([CH3:15])[O:12][C:8]=12

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8148DibutylamineHCID 1190244-Hydroxy-2,3,6-trimethylphenyl acetateHCID 110237212,6,10,14-tetramethylpentadecene

Product 1

HCID 86472Alpha-Tocopherol Acetate

Conditions

Temperature
170 °C

Procedure

A pressure-proof reaction vessel equipped with a stirrer was charged with 7.0 g (0.036 mole) of 4-acetoxy-2,3,5-trimethylphenol, 50.0 g (0.18 mole) of 2,6,10,14-tetramethyl-1-pentadecene, 1.4 g (0.045 mole) of 80% paraformaldehyde, 0.5 g (0.0036 mole) of dibutylamine and 1.1 g (0.018 mole) of acetic acid, and the mixture was reacted, with stirring, at 170° C. for 4 hours.

Workup

  1. customA pressure-proof reaction vessel
  2. customequipped with a stirrer
  3. customthe mixture was reacted

Sources & evidence

ORD record
ord-fe89401249404f6e9baed3e54bacbe04
Source dataset
uspto-grants-1996_02
Patent number
US05495026

Reaction notes

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