2,3-Dihydrofuran → HCID 19019067, compound

HRID 1110095Notes

Reaction equation

HRID 1110095 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[CH2:6].[O:11]1[CH:15]=[CH:14][CH2:13][CH2:12]1>Cl.C(OCC)C>[O:11]1[CH2:12][CH2:13][CH2:14][CH:15]1[O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:12]1[CH2:13][CH2:14][CH2:15][O:11]1)[CH:5]=[CH2:6]

Participants

5

Reactant 2

HCID 709342,3-DihydrofuranHCID 1513983,4-Dihydroxystyrene

Product 1

HCID 19019067HCID 19019067, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

To 38.1 g (0.28 mol) of 3,4-dihydroxystyrene and 118 g (1.68 mol) of 2,3-dihydrofuran are added 5 drops of concentrated hydrochloric acid, whereupon an exothermic reaction ensues. The solution is stirred for 4 h at 50° C. and then poured on to a mixture of ice-water and diethyl ether. After two extractions with diethyl ether, the organic phase is washed three times at 0° C. with 1N NaOH and dried over Na2SO4. The solvent is removed by evaporation to leave a clear liquid which is purified by distillation in a bulb tube (155° C./0.02 torr) or by column chromatography (silica gel, hexane/ethyl acetate 4:1).

Workup

  1. customwhereupon an exothermic reaction
  2. extractionAfter two extractions with diethyl ether
  3. washthe organic phase is washed three times at 0° C. with 1N NaOH
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed by evaporation
  6. customto leave a clear liquid which
  7. distillationis purified by distillation in a bulb tube (155° C./0.02 torr)

Sources & evidence

ORD record
ord-e92d55000f9145878b4ca5da59696b86
Source dataset
uspto-grants-1994_06
Patent number
US05324804

Reaction notes

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