Hydrochloric Acid → HCID 22940147, compound

HRID 2424314Notes

Reaction equation

HRID 2424314 reaction equation
O.Cl.C[O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[CH:8]=[C:7]([CH3:13])[C:6]=1[C:14](=O)[CH3:15].C(SCCC1(O)C(C)=C(C)C=C(C)C1)C>CN(C)C=O>[CH3:11][C:10]1[C:9]([CH3:12])=[CH:8][C:7]([CH3:13])=[C:6]([CH:14]=[CH2:15])[C:5]=1[OH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 22940168HCID 22940168, compoundHCID 86596502HCID 86596502, compound

Product 1

HCID 22940147HCID 22940147, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, in dry N,N-dimethylformamide (8 mL) was suspended 270 mg (6.75 mmol) of 60% sodium hydride, and 0.60 mL (8.10 mmol) of ethanethiol was gradually added dropwise to the suspension. After stirring for 15 minutes, 400 mg (2.27 mmol) of 3-methoxy-1,2,5-trimethyl-4-vinylbenzene obtained in (4) and dissolved in dry N,N-dimethylformamide (1.5 mL) was added to the mixture, and the resulting mixture was refluxed for 1 hour. After cooling to room temperature, the reaction mixture was poured into water, made acidic by adding hydrochloric acid, and extracted with hexane. The organic layers were combined, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (Wako gel C-100, hexane:ethyl acetate=20:1) and by preparative thin-layer chromatography (available from MERCK CO., 1.05744, developed by hexane:ethyl acetate=8:1) to obtain 63.0 mg (0.389 mmol, Yield from 1-(2-methoxy-3,4,6-trimethylphenyl)ethanone: 16.2%) of 2,3,5-trimethyl-6-vinylphenol and 330 mg (1.47 mmol, Yield from 1-(2-methoxy-3,4,6-trimethylphenyl)ethanone: 61.4%) of 2-[1-(ethylsulfanylethyl]-3,5,6-trimethylphenol.

Workup

  1. additionwas added to the mixture
  2. temperaturethe resulting mixture was refluxed for 1 hour
  3. extractionextracted with hexane
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed
  7. customthe residue was purified by silica gel column chromatography (Wako gel C-100, hexane:ethyl acetate=20:1) and by preparative thin-layer chromatography (available from MERCK CO., 1.05744, developed by hexane:ethyl acetate=8:1)
  8. customto obtain

Sources & evidence

ORD record
ord-dc51939879504ed5b64eb5cc12568f20
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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