Hydrochloric Acid → HCID 10659962, compound

HRID 346221Notes

Reaction equation

HRID 346221 reaction equation
[CH2:1]([C:5]1([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15]C)[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].[Br-].[Al+3].[Br-].[Br-].Cl.C(OCC)C>C1C=CC=CC=1>[CH2:1]([C:5]1([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[OH:15])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 166749BromhydrolHCID 106847942,2-dibutyl-3,4-dihydro-5-methoxy-1(2H)naphthalenone

Product 1

HCID 10659962HCID 10659962, compoundYield 119.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2,2-dibutyl-3,4-dihydro-5-methoxy-1(2H)-naphthalenone (2.321 g) and aluminium bromide (7.0 g) in dried benzene (40 ml) was refluxed for 40 minutes and allowed to cool in an ice-water bath. The cooled mixture was poured into a mixture of 1N aqueous hydrochloric acid (150 ml) and diethyl ether (100 ml) with stirring. The organic layer was washed with brine, dried, and concentrated in vacuo to yield 2,2-dibutyl-3,4-dihydro-5-hydroxy-1(2H)-naphthalenone (2.643 g) as a crude syrup.

Workup

  1. temperaturewas refluxed for 40 minutes
  2. temperatureto cool in an ice-water bath
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89402a050d864c85af1b0802f5f4ce74
Source dataset
uspto-grants-1991_10
Patent number
US05061718

Reaction notes

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