Epichlorohydrin → 1-chloro-3-(3-phenyl-3,4-dihydro-2H-1-benzopyrane-7-yloxy)-2-propanol

HRID 1074455Notes

Reaction equation

HRID 1074455 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:10]=3[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1CCCCC1.[Cl:24][CH2:25][CH:26]1[O:28][CH2:27]1>>[Cl:24][CH2:25][CH:26]([OH:28])[CH2:27][O:17][C:15]1[CH:14]=[CH:13][C:11]2[CH2:12][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][O:9][C:10]=2[CH:16]=1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 8082PiperidineHCID 204967613-Phenylchroman-7-ol

Product 1

HCID 204967161-chloro-3-(3-phenyl-3,4-dihydro-2H-1-benzopyrane-7-yloxy)-2-propanol

Procedure

11.3 g 3-phenyl-7-hydroxy-3,4-dihydro-2H-1-benzopyrane, 0.1 cm3 piperidine and 22 cm3 1-chloro-2,3-epoxypropane were stirred at 90° C. for 9 hours. The solution was evaporated under reduced pressure, then twice 60-60 cm3 of benzene were distilled off from the residue, it was dissolved in 50 cm3 of tetrahydrofurane and into the solution hydrochloric gas was introduced for 5 minutes. The solution was evaporated after an hour's standing, and the residue was crystallized from aceton. 10 g 1-chloro-3-(3-phenyl-3,4-dihydro-2H-1-benzopyrane-7-yloxy)-2-propanol (m.p. 74°-76° C.) was obtained.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. distillationtwice 60-60 cm3 of benzene were distilled off from the residue, it
  3. dissolutionwas dissolved in 50 cm3 of tetrahydrofurane and into the solution hydrochloric gas
  4. additionwas introduced for 5 minutes
  5. customThe solution was evaporated after an hour's
  6. customthe residue was crystallized from aceton

Sources & evidence

ORD record
ord-ec6ad1fd9ef4443daf9922b0787e6ae4
Source dataset
uspto-grants-1983_07
Patent number
US04391821

Reaction notes

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