Sulfuric Acid → (4S)-4-hydroxy-2-nonynal

HRID 973338Notes

Reaction equation

HRID 973338 reaction equation
C([O:3][CH:4](OCC)[C:5]#[C:6][C@@H:7]([O:13]C1CCCCO1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])C.O1CCCC1.S(=O)(=O)(O)O>O>[OH:13][C@@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:6]#[C:5][CH:4]=[O:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 68121838(4S)-1,1-diethoxy-4-(2-tetrahydropyranyloxy)-2-nonyne

Product 1

HCID 86735171(4S)-4-hydroxy-2-nonynal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (4S)-1,1-diethoxy-4-(2-tetrahydropyranyloxy)-2-nonyne (96.0 g., 0.31 mole), tetrahydrofuran (500 ml.), and 30% aqueous sulfuric acid (100 ml.) is stirred at room temperature for 17 hours. The solution is diluted with water and the oily product is extracted with ether. The ether extract is washed with sodium bicarbonate solution and water and dried over sodium sulfate. Evaporation of the ether leaves (4S)-4-hydroxy-2-nonynal as a colorless residual oil which is used in the following step without further purification.

Workup

  1. extractionthe oily product is extracted with ether
  2. extractionThe ether extract
  3. washis washed with sodium bicarbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the ether

Sources & evidence

ORD record
ord-5ec0650efd8c43c8a75b3564ee94104e
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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