Triethylamine → Dihydrosafrole

HRID 1439386

Reaction equation

HRID 1439386 reaction equation
[CH2:1](O)[CH2:2][C:3]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][O:6][C:5]=2[CH:4]=1.[CH2:13](N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[CH2:7]1[O:8][C:9]2[CH:10]=[CH:11][C:3]([CH2:2][CH2:1][CH3:13])=[CH:4][C:5]=2[O:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27598462-(1,3-Dioxaindan-5-yl)ethan-1-ol

Product 1

HCID 7197DihydrosafroleYield 140.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Homopiperonyl alcohol (1) (7.03g, 42.4 mmol)1,2,3 and triethylamine (8.59 g., 85.0 mmol) were dissolved in methylene chloride (100 ml). The mixture was cooled to 0°-5°, then methanesulfonyl chloride (7.31 g., 63.6 mmol) was added slowly dropwise to the vigorously stirred solution. The mixture was stirred an additional 30 mins., then transferred to a separatory funnel where it was washed with water (3 × 50 ml), 4% hydrochloric acid (3 × 50 ml), saturated sodium bicarbonate solution (25 ml), saturated brine (25 ml) and dried over sodium sulfate. Filtration and evaporation of the methylene chloride yielded 9.76 g of a brown oil (94%); NMR--(CDCl3) 6.72 (m, 3H), 5.92 (S, 2H), 4.34 (t, J=7, 2H), 2.95 (t, J=7), lying under 2.89 (s) giving a total integration of 5H. This material was used without further purification.

Workup

  1. temperatureThe mixture was cooled to 0°-5°
  2. custom, then transferred to a separatory funnel
  3. washwhere it was washed with water (3 × 50 ml), 4% hydrochloric acid (3 × 50 ml), saturated sodium bicarbonate solution (25 ml), saturated brine (25 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and evaporation of the methylene chloride

Sources & evidence

ORD record
ord-32d23eaea49446be9e9ad320385f767c
Source dataset
uspto-grants-1977_11
Patent number
US04059593

Linked notes

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