Hydrochloric Acid → HCID 57141646, compound

HRID 1381325Notes

Reaction equation

HRID 1381325 reaction equation
[CH3:1][C:2]1[C:7]([O:8][Si](C)(C)C)=[CH:6][CH2:5][C:4]([CH3:14])([CH3:13])[C:3]=1[CH:15]=[CH:16][C:17]([O:21][CH3:22])([CH3:20])[CH:18]=[CH2:19].C(=O)([O-])[OH:24].[Na+].O.O.O.S([O-])([O-])(=O)=O.[Mg+2].C(OO)(=O)C.Cl>CO.C(OCC)C>[OH:24][CH:6]1[CH2:5][C:4]([CH3:14])([CH3:13])[C:3]([CH:15]=[CH:16][C:17]([O:21][CH3:22])([CH3:20])[CH:18]=[CH2:19])=[C:2]([CH3:1])[C:7]1=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6585Peracetic AcidHCID 516892Sodium BicarbonateHCID 22242376Magnesium sulfate trihydrateHCID 54166181HCID 54166181, compound

Product 1

HCID 57141646HCID 57141646, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 32.0 g of 1-[2,6,6-trimethyl-3-(trimethylsiloxy)-1,3-cyclohexadien-1-yl]-3-methoxy-3-methyl-1,4-pentadiene, 10.0 g of sodium hydrogen carbonate, 10.0 g of magnesium sulphate trihydrate and 500 ml of diethyl ether was stirred well at 2°-5° C., then treated dropwise with 26.45 g of 40% peracetic acid and left to warm to room temperature. The mixture was subsequently cooled to 0° C., treated dropwise with 90 ml of a mixture of methanol and 1N hydrochloric acid (vol. 1:1) and extracted with diethyl ether. The organic phase was washed twice with cold semi-concentrated sodium pyrosulphite solution, once with ice-water, twice with ice-water to which had been added a small amount of saturated sodium hydrogen carbonate solution and a further twice with ice-water. After drying over sodium sulphate and concentration under a water-jet vacuum at 35° C., there were obtained 26.4 g of crude 1-(4-hydroxy-3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)- 3-methoxy-3-methyl-1,4-pentadiene (purity 91.5%) which still contained 7.07% of 1-(3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methoxy-3-methyl-1,4-pentadiene.

Workup

  1. waitleft
  2. temperatureThe mixture was subsequently cooled to 0° C.
  3. extractionextracted with diethyl ether
  4. washThe organic phase was washed twice with cold semi-concentrated sodium pyrosulphite solution, once with ice-water, twice with ice-water to which
  5. additionhad been added a small amount of saturated sodium hydrogen carbonate solution
  6. dry with materialAfter drying over sodium sulphate and concentration under a water-jet vacuum at 35° C.

Sources & evidence

ORD record
ord-72d7419752c441ca917f05aca4dabec1
Source dataset
uspto-grants-1986_04
Patent number
US04585885

Reaction notes

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