3,4-Dichlorotoluene-alpha-thiol → 5-(3,4-Dichloro-benzylsulfanylmethyl)-6-hydroxy-3,4-dihydro-2H-naphthalen-1-one

HRID 496397Notes

Reaction equation

HRID 496397 reaction equation
Cl[CH2:2][C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:14].[Cl:15][C:16]1[CH:17]=[C:18]([CH2:23][SH:24])[CH:19]=[CH:20][C:21]=1[Cl:22]>>[Cl:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:23][S:24][CH2:2][C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:14]

Participants

3

Reactant 2

HCID 1189863,4-Dichlorotoluene-alpha-thiolHCID 123936195-(chloromethyl)-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 223246835-(3,4-Dichloro-benzylsulfanylmethyl)-6-hydroxy-3,4-dihydro-2H-naphthalen-1-oneYield 63.5%

Conditions

Temperature
40 °C

Procedure

5-Chloromethyl-6-hydroxy-1-tetralone (315 mg, 1.5 mmol) and (3,4-Dichloro-phenyl)-methanethiol (1.0 mL, 6.0 mmol) were sealed in a 16×120 mm screw capped tube and heated to 40° C. overnight. The excess (3,4-Dichloro-phenyl)-methanethiol was removed in vacuo and the residue was purified by silica gel chromatography (hexanes/ethyl acetate/acetic acid, 58:40:2) to give 350 mg (63%) of the desired product as a tan powder: (LC-MS, APCI) m/z 367/369 [M+H]+.

Workup

  1. customscrew capped tube
  2. customThe excess (3,4-Dichloro-phenyl)-methanethiol was removed in vacuo
  3. customthe residue was purified by silica gel chromatography (hexanes/ethyl acetate/acetic acid, 58:40:2)

Sources & evidence

ORD record
ord-4efb35718e0f4bb7a7cc3565f57f4ab4
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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