Sulfuric Acid → HCID 18606809, compound

HRID 236660Notes

Reaction equation

HRID 236660 reaction equation
[CH3:1][C@@:2]1([CH2:16][CH2:17][OH:18])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([CH3:14])=[C:7]([OH:13])[C:8]=2[CH3:12])[O:3]1.[CH2:19]=[C:20]([CH3:22])[CH3:21].S(=O)(=O)(O)O>C(Cl)Cl>[CH3:1][C@@:2]1([CH2:16][CH2:17][O:18][C:20]([CH3:22])([CH3:21])[CH3:19])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([CH3:14])=[C:7]([OH:13])[C:8]=2[CH3:12])[O:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255Isobutylene2×HCID 642448HCID 642448, compound

Product 1

HCID 18606809HCID 18606809, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g of (S)-2,5,7,8-tetramethyl-6-hydroxy-2-(2-hydroxyethyl)-chroman were suspended in 250 ml of methylene chloride, and isobutene was passed through the suspension. After 15 minutes, 1 ml of concentrated sulfuric acid was added, and stirring was then continued for a further 4 hours at room temperature, while a gentle stream of isobutene was passed through. The mixture was then left to stand overnight in a closed vessel. The organic phase was washed with sodium bicarbonate solution and with water, and was then dried and evaporated down. The crude product was purified over silica gel, using a 5:1 hexane/acetone solvent mixture. 4.5 g of (S)-2,5,7,8-tetramethyl-6-hydroxy-2-(2-tert.-butoxyethyl)-chroman were obtained as a colorless oil. [α]36520 =+4.23° (c=2, ethanol).

Workup

  1. waitThe mixture was then left
  2. waitto stand overnight in a closed vessel
  3. washThe organic phase was washed with sodium bicarbonate solution and with water
  4. customwas then dried
  5. customevaporated down
  6. customThe crude product was purified over silica gel

Sources & evidence

ORD record
ord-bf8731e0e20a47cd8c11af235a3a5629
Source dataset
uspto-grants-1987_02
Patent number
US04645845

Reaction notes

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