Methanol → 6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ol

HRID 2103342Notes

Reaction equation

HRID 2103342 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].CO>O>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([OH:20])[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 590217396-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 575267796-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-olYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-I-one (1.31 g, 4.6 mmol) and sodium borohidride (0.35 g, 9.3 mmol) were added to 50 mL methanol, and the reaction mixture was stirred at room temperature for one hour. Water (200 mL was then added to the reaction mixture, resulting in precipitation of white crystals, which were collected by filtration and dried under N2 to give 1.2 g (4.16 mmol, 90%) of 6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1ol, MS: 289 (M+H)+.

Workup

  1. customresulting in precipitation of white crystals, which
  2. filtrationwere collected by filtration
  3. customdried under N2

Sources & evidence

ORD record
ord-057086cdf5924277ba97725a1736b1c4
Source dataset
uspto-grants-2009_08
Patent number
US07576103B2

Reaction notes

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