Hydrochloric Acid → HCID 178520641, compound

HRID 1243639Notes

Reaction equation

HRID 1243639 reaction equation
[O:1]1[CH:5]=[CH:4][CH2:3][CH2:2]1.Cl.[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]([CH2:21][OH:22])[CH2:19][OH:20])=[CH:10][CH:9]=1>O1CCOCC1.O.ClCCl>[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C@@H:18]2[CH2:21][O:22][C@@H:5]([CH2:4][CH2:3][CH2:2][OH:1])[O:20][CH2:19]2)=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 709342,3-DihydrofuranHCID 21930236HCID 21930236, compound

Product 1

HCID 178520641HCID 178520641, compoundYield 36.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.75 ml (10 mmol) of 2,3-dihydrofuran and then 0.25 ml of a concentrated aqueous hydrochloric acid solution (37%) are added to a solution of 1.18 g (5 mmol) of 2-(4-chloronaphthalen-1-yl)-1,3-propanediol in 10 ml of dioxane. The mixture is allowed to react overnight at ambient temperature and then 5 ml of water are added. The mixture is stirred for 5 hours and is then diluted in 25 ml of water and 50 ml of dichloromethane. The mixture is separated after settling out and the aqueous phase is extracted with 50 ml of dichloromethane. The organic phases are washed with 25 ml of a saturated aqueous sodium chloride solution, drying is carried out over sodium sulfate and concentration is carried out under reduced pressure. The residue is purified by chromatography on silica gel, eluting with a 70/30 and then 60/40 mixture of cyclohexane and ethyl acetate. After recrystallization from diisopropyl ether, 0.557 g of product is obtained, in the form of white crystals.

Workup

  1. customto react overnight at ambient temperature
  2. customThe mixture is separated
  3. extractionthe aqueous phase is extracted with 50 ml of dichloromethane
  4. washThe organic phases are washed with 25 ml of a saturated aqueous sodium chloride solution
  5. customdrying
  6. concentrationis carried out over sodium sulfate and concentration
  7. customThe residue is purified by chromatography on silica gel
  8. washeluting with a 70/30
  9. addition60/40 mixture of cyclohexane and ethyl acetate
  10. customAfter recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-83d05b35d630450380002785bfe31a23
Source dataset
uspto-grants-2006_10
Patent number
US07119116B2

Reaction notes

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