Thiophenol → 7-Hydroxy-2-tetralone

HRID 747948Notes

Reaction equation

HRID 747948 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH2:10]2)=[CH:5][CH:4]=1.C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>O.CN1C(=O)CCC1>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH2:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 777857-Methoxy-2-tetralone

Product 1

HCID 41988757-Hydroxy-2-tetraloneYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

Combine 7-methoxy-2-tetralone (5.00 g, 28.3 mmol), thiophenol (3.39 g, 30.8 mmol), K2CO3 (213 mg, 1.54 mmol), and NMP (15 ml) in a round bottom flask equipped with nitrogen inlet. Heat at 180° C. for six hours and then stir at ambient temperature overnight. Treat reaction mixture with 1N aq. NaOH (20 ml) and water (20 ml) before extracting with Et2O. Adjust the alkaline mixture to pH 4 with 1N aq. HCl and extract with Et2O (3×). Dry (MgSO4) the ethereal layer and concentrate to a yellow solid. Purify the crude material on silica gel, eluting with 5% EtOAc/DCM, to obtain 7-hydroxy-2-tetralone (1.88 g) as a light red solid. 1HNMR (CDCl3): 7.09 (d, 1H), 6.69 (d, 1H), 6.62 (s, 1H), 4.86 (s, 1H), 3.53 (s, 2H), 2.99 (t, 2H), 2.54 (t, 2H).

Workup

  1. additionTreat
  2. extractionbefore extracting with Et2O
  3. extractionextract with Et2O (3×)
  4. dry with materialDry (MgSO4) the ethereal layer
  5. concentrationconcentrate to a yellow solid
  6. customPurify the crude material on silica gel
  7. washeluting with 5% EtOAc/DCM

Sources & evidence

ORD record
ord-23c956b02bfd401b9c9d8217f945c6a9
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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