Hydrochloric Acid → HCID 12138358, compound

HRID 1271668Notes

Reaction equation

HRID 1271668 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:36]=[C:37]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH:38]=1)[CH2:8][S:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([S:20][CH2:21][C:22]2[CH:27]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:25]=[C:24]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:23]=2)[CH:19]=1)[C:13](OC)=[O:14])([CH3:4])([CH3:3])[CH3:2].Cl>C1(C)C=CC=CC=1>[C:32]([C:24]1[CH:23]=[C:22]([CH:27]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:25]=1)[CH2:21][S:20][C:18]1[CH:17]=[C:12]([CH:11]=[C:10]([S:9][CH2:8][C:7]2[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:38]=[C:37]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH:36]=2)[CH:19]=1)[CH2:13][OH:14])([CH3:35])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12138357HCID 12138357, compound

Product 1

HCID 12138358HCID 12138358, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Methyl 3,5-bis(3,5-di-tertiary-butylbenzylthio)benzoate (52.0 g, 86.0 mmol) was dissolved in 300 ml of toluene. To this, was added dropwise a 70% solution of sodium dihydrobis(2-methoxyethoxy)aluminate in toluene (52 g, 180.0 mmol), maintaining the temperature at 35° C. or below and the resulting mixture was stirred for 2 hours under the same conditions. After completion of the reaction, the reaction mixture was poured into 500 ml of a cold 10% hydrochloric acid solution, followed by stirring for 10 minutes. The toluene layer was separated, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was then purified by means of chromatography with dichloromethane, giving 4.96 g of 3,5-bis(3,5-di-tertiary-butylbenzylthio)benzyl alcohol as a viscous substance.

Workup

  1. temperaturemaintaining the temperature at 35° C. or below
  2. customAfter completion of the reaction
  3. stirringby stirring for 10 minutes
  4. customThe toluene layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was then purified by means of chromatography with dichloromethane

Sources & evidence

ORD record
ord-5a614f9d2639440d97c3e78c96e425d4
Source dataset
uspto-grants-2007_04
Patent number
US07205428B2

Reaction notes

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