3,4-dihydro-2H-pyran → HCID 11219861, compound

HRID 258923

Reaction equation

HRID 258923 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([OH:8])[CH3:7])=[CH:4][CH:3]=1.[CH2:11]1[CH2:16][O:15][CH:14]=[CH:13][CH2:12]1>Cl.CCOCC>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([CH3:7])[O:8][CH:14]2[CH2:13][CH2:12][CH2:11][CH2:16][O:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 953521-(4-Bromophenyl)ethanol

Product 1

HCID 11219861HCID 11219861, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 269 parts of p-bromo-α-methylbenzyl alcohol and 225 parts of 2H-3,4-dihydropyran is stirred and cooled to 0° C. Then there are added dropwise 10 drops of concentrated hydrochloric acid solution and the whole is stirred in an ice-bath (room temperature is reached). After stirring for 24 hours, the reaction mixture is poured onto 1200 parts of ether. The organic phase is washed twice with a sodium hydrogen carbonate solution and twice with water, dried, filtered and evaporated. The residue is distilled, yielding 2-(p-bromo-α-methylbenzyloxy)tetrahydropyran; bp. 165°-177° C. at 20 mm. pressure.

Workup

  1. stirringthe whole is stirred in an ice-bath (room temperature is reached)
  2. stirringAfter stirring for 24 hours
  3. washThe organic phase is washed twice with a sodium hydrogen carbonate solution and twice with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. distillationThe residue is distilled

Sources & evidence

ORD record
ord-7de4891e22fe41ca84d1bd5bba4b0925
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Linked notes

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