Hydrochloric Acid → HCID 57740557, compound

HRID 908075Notes

Reaction equation

HRID 908075 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[O:12].[CH2:13]([Mg]Cl)[CH:14]=[CH2:15].Cl.C(OCC)C.[CH2:24]1[CH2:28]OC[CH2:25]1>CCCCCC.C(OCC)(=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:12])([CH2:28][CH:24]=[CH2:25])[CH2:13][CH:14]=[CH2:15]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 62012-NaphthalenecarboxaldehydeHCID 8028Tetrahydrofuran2×HCID 178418473HCID 178418473, compound

Product 1

HCID 57740557HCID 57740557, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

First, 16 g of 2-naphthaldehyde was dissolved in 150 mL of THF, and 150 mL of allyl magnesium chloride (a 2.0 M THF solution) was slowly added thereto. The resulting mixture was reacted at a temperature of about 45° C. for 8 hours. After the reaction, the reactant was slowly neutralized in an extreme amount of thin hydrochloric acid solution. Then, the extract was extracted therefrom using diethyl ether and purified through column chromatography (hexane:ethyl acetate=3:1), preparing 10 g of 4-(naphthalen-2yl)hepta-1,6-dien-4-ol monomer (yield: 42%).

Workup

  1. customThe resulting mixture was reacted at a temperature of about 45° C. for 8 hours
  2. customAfter the reaction
  3. extractionThen, the extract was extracted

Sources & evidence

ORD record
ord-ad0a90302bfd4fd5b503430809e488db
Source dataset
uspto-grants-2011_09
Patent number
US08017301B2

Reaction notes

Loading…