Mercaptoethanesulfonic acid → 1,1,4,4-Tetramethyltetralin

HRID 1781216

Reaction equation

HRID 1781216 reaction equation
BrCC([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]2([CH3:18])[CH3:17])=O.SCCS(O)(=O)=O.[Na:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C1COCC1.O.C(OCC)(=O)C>[Na:26].[CH3:17][C:8]1([CH3:18])[C:7]2[C:12](=[CH:13][CH:14]=[CH:5][CH:6]=2)[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9]1

Participants

10

Reactant 4

HCID 598Mercaptoethanesulfonic acidHCID 11430Potassium CarbonateHCID 28013372-Bromo-1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-oneHCID 5360545Sodium

Product 2

HCID 811861,1,4,4-TetramethyltetralinHCID 5360545Sodium

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(bromoacetyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (12) (15.5 mg, 0.050 mmol) in DMF (0.13 mL) and THF (0.13 mL) was added a freshly prepared solution of 2-mercapto-1-ethanesulfonic acid, sodium salt (2) (25 mg, 0.15 mmol) and potassium carbonate (21 mg, 0.15 mmol) in water (0.15 mL) at room temperature. The resulting biphasic mixture was stirred for 30 min. The reaction mixture was diluted with ethyl acetate (2.5 mL), and the organic layer was separated, washed with water (2×1 mL) and brine (1×1 mL), dried and concentrated to afford 6-[2'-mercapto-1'-ethanesulfonic acid, sodium salt)acetyl]-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (20) as a solid. 1H NMR (pyr-d5): δ 8.19, 7.90, 7.40 (m, 3H), 4.11 (s, 2H), 3.5 (m, 4H), 1.55 (s, 4H), 1.20 (d, 12H).

Workup

  1. customthe organic layer was separated
  2. washwashed with water (2×1 mL) and brine (1×1 mL)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bd07e98aceef4b509d4e39b6ba9624c9
Source dataset
uspto-grants-1997_05
Patent number
US05632898

Linked notes

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