Potassium Hydroxide → 4,4-Dimethyl-7-[(dimethylamino)thiocarbonyloxy]-1-tetralone

HRID 53275

Reaction equation

HRID 53275 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[C:5](=[O:13])[CH2:4][CH2:3]1.[OH-].[K+].[CH3:17][N:18]([CH3:22])[C:19](Cl)=[S:20]>O.O1CCCC1>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][C:8]([O:12][C:19]([N:18]([CH3:22])[CH3:17])=[S:20])=[CH:9][CH:10]=2)[C:5](=[O:13])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 27871Dimethylthiocarbamoyl chlorideHCID 221018653,4-Dihydro-7-hydroxy-4,4-dimethyl-1(2H)-naphthalenone

Product 1

HCID 537168184,4-Dimethyl-7-[(dimethylamino)thiocarbonyloxy]-1-tetralone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,4-dimethyl-7-hydroxy-1-tetralone (XIV) (3.07 g, 16.16 mmol) in water (10.77 mL) containing potassium hydroxide (904 mg) cooled below 10° C. was added N,N-dimethylthiocarbamoyl chloride (2.67 g, 21.6 mmol) in tetrahydrofuran (4.30 mL); the reaction temperature kept below 12° C. After 10 minutes, reaction mixture is made basic by the addition of a 10% aqueous KOH solution (5.39 mL). Product is extracted with ethyl acetate (2×50 mL), organic phases concentrated in vacuo and the residue chromatographed on silica gel (eluted with 10% ethyl acetate in hexane) to give 3.74 g (Y: 84%) of title product; 1H-NMR (CDCl3): δ7.68 (d, J=2.6 Hz, 1H), 7.45 (d, J=8.5 Hz, 1H), 7.27 (dd, J=8.5, 2.6 Hz, 1H), 3.46 (s, 3H), 3.34 (s, 3H), 2.73 (t, J=6.8 Hz, 2H), 2.04 (t, J=6.8 Hz, 2H), 1.41 (s, 6H); MS (DCI) m/e: 278 (MH+).

Workup

  1. temperaturecooled below 10° C.
  2. customkept below 12° C
  3. customreaction mixture
  4. extractionProduct is extracted with ethyl acetate (2×50 mL), organic phases
  5. concentrationconcentrated in vacuo
  6. customthe residue chromatographed on silica gel (eluted with 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-47473cc55f5644b6b19ec0dd75be0af0
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Linked notes

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