Water → 4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone

HRID 2051585Notes

Reaction equation

HRID 2051585 reaction equation
[Br-].[Al+3].[Br-].[Br-].[C:5]1([OH:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.O.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24]>>[Cl:17][C:18]1[CH:23]=[C:22]([CH:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5](=[O:15])[CH2:6][CH2:7]2)[CH:21]=[CH:20][C:19]=1[Cl:24]

Participants

5

Reactant 4

HCID 962WaterHCID 70051-NaphtholHCID 72391,2-DichlorobenzeneHCID 166749Bromhydrol

Product 1

HCID 37462514-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenoneYield 79.6%

Conditions

Temperature
65 °C

Procedure

In a solution of 100 g (0.374 mole) of anhydrous aluminium bromide in 130 ml of orthodichlorobenzene, 28 g (0.194 mole) of α-naphthol are added. The green solution obtained is heated for 1 hour at 65° C. then hydrolysed with 400 ml of water at 40° C. After decantation, the organic phase is separated which is concentrated under a vacuum. After crystallization of the residue in 140 ml of methanol at 0° C. for 2 hours, 45 g of the expected compound are obtained after filtration and drying.

Workup

  1. customThe green solution obtained
  2. customAfter decantation, the organic phase is separated which
  3. concentrationis concentrated under a vacuum
  4. customAfter crystallization of the residue in 140 ml of methanol at 0° C. for 2 hours

Sources & evidence

ORD record
ord-413ef1b89ef24875977f256dd731837c
Source dataset
uspto-grants-1991_05
Patent number
US05019655

Reaction notes

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