Acetic Anhydride → Phytyltrimethylhydroquinone diacetate

HRID 1685906Notes

Reaction equation

HRID 1685906 reaction equation
[CH2:1]([C:21]1[C:26]([OH:27])=[C:25]([CH3:28])[C:24]([CH3:29])=[C:23]([OH:30])[C:22]=1[CH3:31])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH2:7][C@@H:8]([CH2:10][CH2:11][CH2:12][C@@H:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])\[CH3:4].[C:32]([O:35]C(=O)C)(=[O:34])[CH3:33]>N1C=CC=CC=1>[C:32]([OH:35])(=[O:34])[CH3:33].[C:32]([OH:35])(=[O:34])[CH3:33].[CH2:1]([C:21]1[C:26]([OH:27])=[C:25]([CH3:28])[C:24]([CH3:29])=[C:23]([OH:30])[C:22]=1[CH3:31])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH2:7][C@@H:8]([CH2:10][CH2:11][CH2:12][C@@H:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:19])[CH3:20])[CH3:14])[CH3:9])\[CH3:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 87503419Phytyltrimethylhydroquinone

Product 1

HCID 131724363Phytyltrimethylhydroquinone diacetateYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The crude phytyltrimethylhydroquinone (31, 9 g, 20.1 mmol) was dissolved in dry pyridine (90 g) and acetic anhydride (90 g). After storage for 10 h at room temperature, the mixture was poured onto ice (200 mL) and extracted with ether (2×100 mL). The ether solution was washed with 3N sulfuric acid (2×100 mL), 10% sodium bicarbonate solution (2×100 mL), and again water (2×100 mL), dried (Na2SO4), and evaporated to yield 10.2 g (95%) of diacetate (32) as a light yellow oil. The oil was used in the next step without further purification.

Workup

  1. additionthe mixture was poured onto ice (200 mL)
  2. extractionextracted with ether (2×100 mL)
  3. washThe ether solution was washed with 3N sulfuric acid (2×100 mL), 10% sodium bicarbonate solution (2×100 mL), and again water (2×100 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-da8da63efe49419bb9715aaed8a21b41
Source dataset
uspto-grants-2012_04
Patent number
US08148424B2

Reaction notes

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