Hydrochloric Acid → 4-(3-Benzyloxyphenyl)-4-hydroxy-2,6-dimethyltetrahydropyran

HRID 1653769Notes

Reaction equation

HRID 1653769 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH2:5][CH:4]([CH3:9])[O:3]1.[CH2:10]([O:17][C:18]1[CH:19]=[C:20]([Mg]Br)[CH:21]=[CH:22][CH:23]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OC1C=C(Br)C=CC=1)C1C=CC=CC=1.[Mg].Cl>O1CCCC1>[CH2:10]([O:17][C:18]1[CH:23]=[C:22]([C:6]2([OH:8])[CH2:5][CH:4]([CH3:9])[O:3][CH:2]([CH3:1])[CH2:7]2)[CH:21]=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 70626Tetrahydro-2,6-dimethyl-4H-pyran-4-oneHCID 27566381-(Benzyloxy)-3-bromobenzeneHCID 5462224MagnesiumHCID 178419633HCID 178419633, compound

Product 1

HCID 200806044-(3-Benzyloxyphenyl)-4-hydroxy-2,6-dimethyltetrahydropyran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2,6-dimethyltetrahydropyran-4-one (2.2 g) in tetrahydrofuran (5 ml) was added to a solution of 3-benzyloxyphenylmagnesium bromide [prepared by heating a mixture of 3-benzyloxybromobenzene (5 g), magnesium (0.5 g) and tetrahydrofuran (20 ml)] in tetrahydrofuran and the mixture was stirred at ambient temperature for 3 hours. The mixture was cooled to 5° C., ice (5 ml) and 2N hydrochloric acid solution (25 ml) were added, and the mixture was extracted with ethyl acetate. The organic phase was washed with a saturated sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of toluene and ethyl acetate as eluent. There were thus obtained two isomers of 4-(3-benzyloxyphenyl)-4-hydroxy-2,6-dimethyltetrahydropyran:

Workup

  1. customprepared
  2. temperatureby heating
  3. temperatureThe mixture was cooled to 5° C.
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with a saturated sodium chloride solution
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by column chromatography
  9. temperatureusing increasingly polar mixtures of toluene and ethyl acetate as eluent

Sources & evidence

ORD record
ord-906149dd2a2c493993225db3ec154ca4
Source dataset
uspto-grants-1995_04
Patent number
US05403859

Reaction notes

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