3,4-dihydro-2H-pyran → 2-(m-Bromo-alpha-methylbenzyloxy)tetrahydropyran

HRID 1439548Notes

Reaction equation

HRID 1439548 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH:5]([OH:7])[CH3:6].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])O.[Na+]>Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH:5]([CH3:6])[O:7][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 984791-(3-Bromophenyl)ethanolHCID 516892Sodium Bicarbonate

Product 1

HCID 213917462-(m-Bromo-alpha-methylbenzyloxy)tetrahydropyran

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 20 parts of m-bromo-α-methylbenzylalcohol and 16.8 parts of 3,4-dihydropyran is cooled in an ice-bath and there are added 2 drops of hydrochloric acid solution. The whole is stirred overnight at 0° C and then allowed to come to room temperature. The mixture is poured onto ether and shaken successively with a sodium hydrogen carbonate solution and twice with water. The organic layer is separated, dried, filtered and evaporated. The residue is distilled, yielding 2-(m-bromo-α-methylbenzyloxy)tetrahydropyran; bp. 168°-169° C at 12 mm. pressure.

Workup

  1. temperatureis cooled in an ice-bath
  2. customto come to room temperature
  3. additionThe mixture is poured onto ether
  4. customThe organic layer is separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue is distilled

Sources & evidence

ORD record
ord-dd11fe53a3f34484b7924c4c24723324
Source dataset
uspto-grants-1977_11
Patent number
US04060528

Reaction notes

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