Benzenesulfinic acid → HCID 57141301, compound

HRID 374354Notes

Reaction equation

HRID 374354 reaction equation
[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[C:5]([CH:10]=[CH:11][C:12]([CH3:20])(O[Si](C)(C)C)[CH:13]=[CH2:14])=[C:4]([CH3:21])[C:3]1=[O:22].[C:23]1([S:29]([OH:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Na]>C(O)(=O)C>[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[C:5]([CH:10]=[CH:11][C:12]([CH3:20])=[CH:13][CH2:14][S:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])=[C:4]([CH3:21])[C:3]1=[O:22]

Participants

5

Reactant 3

HCID 12057Benzenesulfinic acidHCID 5360545SodiumHCID 57014248HCID 57014248, compound

Product 1

HCID 57141301HCID 57141301, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(4-hydroxy-3-oxo-2,6,6-trimethyl-1-cyclo- hexen-1-yl)-3-methyl-3-trimethylsiloxy-1,4-pentadiene (200 mg, 0.62 mmol) in 1 ml glacial acetic acid is added benzenesulfinic acid, sodium salt (153 mg, 0.93 mmoles) and the mixture is stirred overnight at ambient temperature. The mixture is concentrated in vacuo and the remanecens is taken up in 10 ml diethylether and 10 ml 1M sodium hydroxide. The aqueous layer is separated and extracted twice with 10 ml diethylether. The combined ether phases are dried and concentrated in vacuo yielding the title compound as a slightly yellow oil.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customThe aqueous layer is separated
  3. extractionextracted twice with 10 ml diethylether
  4. dry with materialThe combined ether phases are dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43c19b7f2ba04507ab4e2f912223c243
Source dataset
uspto-grants-1992_11
Patent number
US05166441

Reaction notes

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