Hydrochloric Acid → HCID 13946744, compound

HRID 259993Notes

Reaction equation

HRID 259993 reaction equation
I[C:2](=[CH2:16])[CH2:3][CH:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[OH:5].[OH-].[Na+].Cl>CN(C)C=O>[C:6]1([CH:4]([CH2:3][C:2]#[CH:16])[OH:5])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22404492HCID 22404492, compound

Product 1

HCID 13946744HCID 13946744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.00 Grams of 2-iodoallyl-α-naphthylcarbinol were dissolved in 50 g of dimethylformamide, and 1.23 g of sodium hydroxide in a flake form were added. The mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction mixture was neutralized with concentrated hydrochloric acid, insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The concentration residue was subjected to extraction with toluene and washed with a 7% sodium carbonate aqueous solution, and then the toluene was distilled off under reduced pressure to give 2.78 g of α-naphthylpropargylcarbinol; nD25 =1.549, FI-MS m/e 196(M+).

Workup

  1. filtrationwere filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionThe concentration residue was subjected to extraction with toluene
  4. washwashed with a 7% sodium carbonate aqueous solution
  5. distillationthe toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-985e063dc8e149d1a7209536c1713cb8
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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