Hydrochloric Acid → trans 4-(2-Chloro-prop-2-yl)-5-hydroxy-tetrahydrofuran-2-one

HRID 326013Notes

Reaction equation

HRID 326013 reaction equation
[CH:1]([C:3](=[C:8]([CH3:10])[CH3:9])[CH2:4][C:5]([OH:7])=[O:6])=[O:2].CCOCC.[Cl-:16].[Li+].Cl>O>[Cl:16][C:8]([C@H:3]1[C@H:1]([OH:2])[O:6][C:5](=[O:7])[CH2:4]1)([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 433294Lithium ChlorideHCID 128824154-Methyl-3-formyl-pent-3-en-1-oic acid

Product 1

HCID 12882418trans 4-(2-Chloro-prop-2-yl)-5-hydroxy-tetrahydrofuran-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1 g of 3-formyl-4-methyl-pent-3-ene-1-oic acid, 25 ml of anhydrous ether and 1 g of lithium chloride was stirred under a current of gaseous hydrogen chloride at -30° C. for 2 hours and then for 2 hours at 0° C. after which the gaseous hydrogen chloride was shut off. The mixture was stirred at room temperature for 48 hours and after 54 hours of contact, the mixture was poured into iced water. The decanted aqueous phase was extracted with benzene and the organic phase was dried and evaporated to dryness under reduced pressure. The 1.1 g of residue was chromatographed over silica gel and was eluted with a 1-1 benzene-ethyl acetate mixture to obtain 545 mg of crystalline (dl trans 4-(2-chloro-prop-2-yl)-5-hydroxy-tetrahydrofuran-2one melting at 80° C.

Workup

  1. extractionThe decanted aqueous phase was extracted with benzene
  2. customthe organic phase was dried
  3. customevaporated to dryness under reduced pressure
  4. customThe 1.1 g of residue was chromatographed over silica gel
  5. washwas eluted with a 1-1 benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-618f6f46ccc748cabeb8dbc120f1d028
Source dataset
uspto-grants-1984_04
Patent number
US04443617

Reaction notes

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