Sulfuric Acid → 2-Allyloxy-tetrahydro-furan

HRID 1656670Notes

Reaction equation

HRID 1656670 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]=[O:6].[CH2:7](O)[CH:8]=[CH2:9].S(=O)(=O)(O)O>CCCCCC>[CH2:9]([O:6][CH:5]1[CH2:4][CH2:3][CH2:2][O:1]1)[CH:8]=[CH2:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7858Allyl AlcoholHCID 930934-Hydroxybutanal

Product 1

HCID 5243812-Allyloxy-tetrahydro-furanYield 70%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The procedure of Example 1 is followed with 4-hydroxybutanal (250 g of 11.0 wt. % solution, 0.31 mol, 1.0 eq.), allyl alcohol (13.8 g, 0.24 mol, 0.80 eq.), and hexanes (500 mL). Concentrated sulfuric acid (0.5 mL) is used in place of the ion-exchange resin. After stirring for 18 h at room temperature the hexane phase contains 5.96% of 2-allyloxytetrahydrofuran (21.3 g, 70% yield). The aqueous phase contains 5.3% of 4-hydroxybutanal and 1.9% of allyl alcohol.

Sources & evidence

ORD record
ord-5e97a6f6a5d2400d81fd658a9dd18e0d
Source dataset
uspto-grants-1993_10
Patent number
US05254702

Reaction notes

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