Hydrochloric Acid → HCID 13946744, compound

HRID 256742Notes

Reaction equation

HRID 256742 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 disolved 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-4dd569f9ff804d09a2bde8f590e9ffb7
Source dataset
uspto-grants-1993_11
Patent number
US05258529

Reaction notes

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