Water → HCID 14235006, compound

HRID 2351849Notes

Reaction equation

HRID 2351849 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:5]([OH:18])=[CH:6][C:7]2[C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1.[CH3:19][N:20]([CH3:24])[C:21](Cl)=[S:22].O>CN(C=O)C>[CH3:19][N:20]([CH3:24])[C:21]([O:18][C:5]1[C:4]([CH3:3])=[CH:13][C:12]2[C:11]([CH3:14])([CH3:15])[CH2:10][CH2:9][C:8]([CH3:17])([CH3:16])[C:7]=2[CH:6]=1)=[S:22]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 2266903,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 14235006HCID 14235006, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

In a round bottom flask there are introduced 1.7 g (57 mmoles) of sodium hydride (80% in oil) and 50 ml of dimethylformamide. There is slowly added a solution of 10.3 g (47 mmoles) of 3-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol in 100 ml of DMF and the reaction mixture is stirred until the cessation of gas evolvement. There are then added 8.1 g (66 mmoles) of dimethylthio-carbamoylchloride in 100 ml of DMF and the reaction mixture is stirred for 4 hours at ambient temperature. The reaction mixture is poured into water and extracted with ethylether. The organic phase is decanted, washed with water, dried on MgSO4 and the solvent evaporated. The residue is purified by chromatography on a silica column (eluant: 20/80 mixture of CH2Cl2 /hexane). 13.2 g (92%) of 2-(N,N-dimethylthiocarbamoyloxy)-3-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene which melts at 102-103° C. are recovered.

Workup

  1. stirringthe reaction mixture is stirred for 4 hours at ambient temperature
  2. extractionextracted with ethylether
  3. customThe organic phase is decanted
  4. washwashed with water
  5. customdried on MgSO4
  6. customthe solvent evaporated
  7. customThe residue is purified by chromatography on a silica column (eluant: 20/80 mixture of CH2Cl2 /hexane)
  8. custom13.2 g (92%) of 2-(N,N-dimethylthiocarbamoyloxy)-3-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene which melts at 102-103° C. are recovered

Sources & evidence

ORD record
ord-1c3515f89e12456b9a157ecee9c0058f
Source dataset
uspto-grants-1989_10
Patent number
US04874747

Reaction notes

Loading…