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

HRID 1452471Notes

Reaction equation

HRID 1452471 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 347.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-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 crystalls, 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- 1-ol, MS: 289 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-97d911fc33984cbb8bdde055b19074ed
Source dataset
uspto-grants-2009_01
Patent number
US07473690B2

Reaction notes

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