Hydrochloric Acid → HCID 22324850, compound

HRID 2210087Notes

Reaction equation

C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9][CH2:8]2)C=C.Cl.CCOCC.C(N(CC)[C:25]1[CH:30]=CC=C[CH:26]=1)C>>[OH:4][C:5]1[C:6]([CH2:30][CH:25]=[CH2:26])=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9][CH2:8]2

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 3283Diethyl Ether

HCID 7061N,N-Diethylaniline

HCID 117012341(2H)-Naphthalenone, 3,4-dihydro-6-(2-propenyloxy)-

Product 1

HCID 22324850HCID 22324850, compoundYield 60%

Procedure

A solution of 12.51 g (61.93 mmol) of 3,4-dihydro-6-(2-propenyloxy)-1(2H)-naphthalenone in 125 mL of N,N-diethylaniline was stirred and heated in a 225°-230° C. oil bath, for 20.5 hr. The resulting dark-amber solution was cooled and poured into 300 mL of cold 3N HCl. The mixture was worked-up with ether in the usual manner giving 12.29 g of a yellow solid which was a mixture of the 5- and 7-allyl isomeric hydroxy naphthalenones. This material was recrystallized from ethyl acetate giving the pure 5-allyl isomer in 60% yield, in several crops. The analytical specimen was a yellow solid, mp 145°-148° C.

Workup

temperatureheated in a 225°-230° C. oil bath
temperatureThe resulting dark-amber solution was cooled

Sources & evidence

ORD record: ord-ac46127a480f4a75b3edf0a23e8166cf
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05457124

Reaction notes

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