Hydrochloric Acid → 5-Hexene-1,2,3-triol

HRID 1600138Notes

Reaction equation

HRID 1600138 reaction equation
CC1(C)[O:6][CH:5]([CH:7]([CH2:9][CH:10]=[CH2:11])[OH:8])[CH2:4][O:3]1.Cl.C(Cl)(Cl)Cl>O1CCCC1>[CH2:4]([OH:3])[CH:5]([OH:6])[CH:7]([OH:8])[CH2:9][CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 126415322,2-Dimethyl-alpha-2-propenyl-1,3-dioxolane-4-methanol

Product 1

HCID 112979875-Hexene-1,2,3-triol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11 g of [R-(R*,R*)]-2,2-dimethyl-alpha-2-propenyl-1,3-dioxolane-4-methanol, prepared by the procedure described in J. Am. Chem. Soc., 1985, 107(26), 8186-8190, in 300 ml of 1:1 tetrahydrofuran: 2N hydrochloric acid is heated at the reflux temperature of the solvents for 2 hours. Chloroform is added and the layers are separated. The aqueous layer is re-extracted 2X with chloroform. The aqueous layer is neutralized with potassium carbonate and exhaustively extracted with 80% chloroform/iso-propanol. Thecombined organic layers are concentrated in vacuo to give 7.51 g of the desired product.

Workup

  1. customthe layers are separated
  2. extractionThe aqueous layer is re-extracted 2X with chloroform
  3. extractionexhaustively extracted with 80% chloroform/iso-propanol
  4. concentrationThecombined organic layers are concentrated in vacuo

Sources & evidence

ORD record
ord-274fb1655ec945eea31aa375d8b09370
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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