Hydrochloric Acid → 3,5-Bis(2-tetrahydropyranyloxy)styrene

HRID 1110097Notes

Reaction equation

HRID 1110097 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([OH:11])[CH:10]=1)[CH:6]=[CH2:7].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)[CH:10]=1)[CH:6]=[CH2:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 121640631,3-Benzenediol, 5-ethenyl-

Product 1

HCID 190190653,5-Bis(2-tetrahydropyranyloxy)styreneYield 62%

Conditions

Temperature
40 °C

Procedure

0.5 ml of concentrated hydrochloric acid is added to 80 g (587 mmol) of 3,5-dihydroxystyrene in 300 g of dihydropyran and the reaction mixture is stirred for 2 h at 40° C. The mixture is then poured into ice-water and extracted twice with ether. The organic phase is washed three times at 0° C. with 1N NaOH, dried, and concentrated by evaporation. The residue is purified by column chromatography (silica gel, hexane/ethyl acetate 4:1), giving 110 g (62%) of a viscous liquid.

Workup

  1. extractionextracted twice with ether
  2. washThe organic phase is washed three times at 0° C. with 1N NaOH
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customThe residue is purified by column chromatography (silica gel, hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-e614a96bd1534259a8571c8e7eb00ca0
Source dataset
uspto-grants-1994_06
Patent number
US05324804

Reaction notes

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