Hydrochloric Acid → HCID 12906158, compound

HRID 647054Notes

Reaction equation

HRID 647054 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].[O]N(S(=O)([O-])=O)S(=O)([O-])=[O:21].[K+].[K+].Cl>[OH-].[Na+]>[CH3:8][C:7]1[C:2](=[O:1])[C:3]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH3:10])[C:5](=[O:21])[C:6]=1[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3032624Potassium nitrosodisulfonateHCID 12906147HCID 12906147, compound

Product 1

HCID 12906158HCID 12906158, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(2'-hydroxy-3',4',6'-trimethylphenyl)hexanol (formula III-2, wherein R=H3C, X=H, Y=OH, n=4, in the free form) (0.02 part) in 1% sodium hydroxide solution (25 parts) was added Fremy's salt (0.2 part) at room temperature with stirring. After being stirred for 1 hour, the mixture was cooled to 0° C., acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give 2,3,5-trimethyl-6-(6'-hydroxyhexyl)-1,4-benzoquinone (formula IV-2 wherein R=H3C, n=4, in the free form) (0.02 part) as yellow needles melting at 43°-45° C.

Workup

  1. stirringAfter being stirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd951038b79c42259651f1a55c50cab2
Source dataset
uspto-grants-1983_10
Patent number
US04407757

Reaction notes

Loading…