3-Chlorocyclopent-1-ene → HCID 70488488, compound

HRID 2413206Notes

Reaction equation

HRID 2413206 reaction equation
[Mg].Cl[CH:3]1[CH2:7][CH2:6][CH:5]=[CH:4]1.[CH:8](=[O:14])[C:9]1[O:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+]>O1CCCC1>[C:5]1([C:9]2([CH2:8][OH:14])[CH2:10][CH:11]=[CH:12][O:13]2)[CH2:6][CH2:7][CH2:3][CH:4]=1

Participants

6

Reactant 4

HCID 72973-Chlorocyclopent-1-eneHCID 7362FurfuralHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 70488488HCID 70488488, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
20 °C

Procedure

Magnesium (36 g, 1.5 mole) and tetrahydrofuran (THF) (300 ml) were added to a reactor, and a solution of 3-chloro-1-cyclopentene (184.5 g, 1.8 mole) in THF (200 ml) was added dropwise at 0° to 10° C. to prepare a Grignard reagent. Thereafter, to this THF solution of the Grignard reagent was added dropwise a solution of furfural (106 g, 1.1 mole) in THF (150 ml) at 0° to 10° C. over about 1 hour, followed by stirring at 20° C. for further 2 hours. After completion of the reaction, the reaction solution was poured into an aqueous ammonium chloride solution (about 1 liter), followed by extraction with ether. The extract was washed with water, dried and concentrated. The residue obtained was distilled under reduced pressure to obtain 135 g (yield, 75%) of pure 2-cyclopentenyl-2-furyl methanol having a boiling point of 80°-86° C./3 mmHg.

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with ether
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue obtained
  7. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-1ae3fb6205b545f7b57cf643bfe09e90
Source dataset
uspto-grants-1985_01
Patent number
US04496586

Reaction notes

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