Hydrochloric Acid → HCID 53679835, compound

HRID 259984Notes

Reaction equation

HRID 259984 reaction equation
I[C:2](=C)[CH2:3][CH2:4][CH:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[OH:6].[OH-].[Na+].Cl.[CH3:21]N(C)C=O>>[CH3:21][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)([CH2:4][C:3]#[CH:2])[OH:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 54508822HCID 54508822, compound

Product 1

HCID 53679835HCID 53679835, compound

Procedure

5.00 Grams of 2-iodoallylmethyl-α-naphthylcarbinol were dissolved in 50 g of dimethylformamide, and 1.18 g of sodium hydroxide in a flake form were added. The resultant mixture was stirred at room temperature for 8 hours. After the reaction was completed, the reaction mixture was neutralized with concentrated hydrochloric acid, insolubles were filtered off, and the remaining filtrate was concentrated under reduced pressure. The concentration residue was subjected to extraction with toluene, and washed with a 7% sodium carbonate aqueous solution. Then, the toluene was distilled off under reduced pressure to give 2.77 g of methyl-α-naphthylpropargylcarbinol; nD25 =1.5141, FI-MS m/e 210 (M) (Propargyl compound/allene compound 100.0/0.0).

Workup

  1. filtrationwere filtered off
  2. concentrationthe remaining 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. distillationThen, the toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-381a1f30382e4bdcaa2bc1666127d89f
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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