Sulfuric Acid → Trimethyl(3,7,11,15-tetramethyl-3-benzamidohexadecyl)hydroquinone Diacetate

HRID 1183226Notes

Reaction equation

HRID 1183226 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:10].[C:14]([OH:17])(=[O:16])[CH3:15].[C:18]([OH:21])(=[O:20])[CH3:19].[CH2:22]([C:42]1[C:47]([OH:48])=[C:46]([CH3:49])[C:45]([CH3:50])=[C:44]([OH:51])[C:43]=1[CH3:52])/[CH:23]=[C:24](/[CH2:26][CH2:27][CH2:28][C@@H:29]([CH2:31][CH2:32][CH2:33][C@@H:34]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH3:35])[CH3:30])\[CH3:25]>C(O)(=O)C>[C:14]([OH:17])(=[O:16])[CH3:15].[C:18]([OH:21])(=[O:20])[CH3:19].[CH3:49][C:46]1[C:47]([OH:48])=[C:42]([CH2:22][CH2:23][C:24]([CH3:25])([NH:8][C:1](=[O:10])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:26][CH2:27][CH2:28][CH:29]([CH3:30])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:35])[CH2:36][CH2:37][CH2:38][CH:39]([CH3:40])[CH3:41])[C:43]([CH3:52])=[C:44]([OH:51])[C:45]=1[CH3:50]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7505BenzonitrileHCID 131724363Phytyltrimethylhydroquinone diacetate

Product 1

HCID 131724364Trimethyl(3,7,11,15-tetramethyl-3-benzamidohexadecyl)hydroquinone DiacetateYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of benzonitrile (10 g, 96.97 mmol), concentrated sulfuric acid (10 g) and glacial acetic acid (40 mL) was added, with stirring at 0° C., the diacetate (32, 10 g, 19.43 mmol). The solution was stored for 10 h at room temperature, then poured onto ice (150 mL) and extracted with ether (3×100 mL). The ether extracts were washed neutral with water (3×100 mL), and saturated sodium bicarbonate solution, dried (Na2SO4) and evaporated in vacuo. The crude product (21 g) was chromatographed on silica gel eluting with petroleum ether:ether (9:1). The unchanged benzonitrile was first removed. Elution with ether then afforded 11 g (88%) of product which was crystallized from petroleum ether to give analytical sample (33) m.p. 90-92° C. (lit.1 94-95° C.).

Workup

  1. additionwas added
  2. additionpoured onto ice (150 mL)
  3. extractionextracted with ether (3×100 mL)
  4. washThe ether extracts were washed neutral with water (3×100 mL), and saturated sodium bicarbonate solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe crude product (21 g) was chromatographed on silica gel eluting with petroleum ether:ether (9:1)
  8. customThe unchanged benzonitrile was first removed
  9. washElution with ether

Sources & evidence

ORD record
ord-c19fc689a61540e6b609e156ae58c754
Source dataset
uspto-grants-2014_03
Patent number
US08664264B2

Reaction notes

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