Hydroquinone → HCID 66968668, compound

HRID 1522693Notes

Reaction equation

HRID 1522693 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:20]=[CH:19][C:11]([O:12]C2CCCCO2)=[CH:10][CH:9]=1.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1(C=CC(O)=CC=1)O>C(Cl)Cl>[C:8]1([CH:20]=[CH:19][C:11]([OH:12])=[CH:10][CH:9]=1)[OH:7].[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 80803,4-dihydro-2H-pyranHCID 2973612,2'-[1,4-Phenylenebis(oxy)]bis(oxane)HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 66968668HCID 66968668, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Another functionalization substance may be 2-[2-(undec-10-enyl)-4-(tetrahydro-2H-pyran-2-yloxy) phenoxy]tetrahydro-H-pyran. This molecule, whose structure is shown in FIG. 13, may be synthesized from 2-[4-(tetrahydro-2H-pyran-2-yloxy) phenoxy]tetrahydro-2H-pyran using any prior art process. The intermediate may be synthesized by first adding dihydropyran (0.83 mL, 9.1 mmol) and pyridinium p-toluenesulfonate (0.11 g, 0.45 mmol) to a solution of hydroquinone (0.25 g, 2.3 mmol) in CH2Cl2 (3 mL). This reaction mixture is then stirred for about 12 hours and diluted with 10 mL of CH2Cl2. The mixture is subsequently washed by 3×5 mL of NaHCO3 and 1×5 mL brine, dried over MgSO4, and concentrated to a white solid. Silica gel chromatography (4:1 hexane/ethyl acetate) provides the di-tetrahydropyran hydroquinone as a white solid (0.48 mg, 75%).

Workup

  1. customThe intermediate may be synthesized
  2. washThe mixture is subsequently washed by 3×5 mL of NaHCO3 and 1×5 mL brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-a2cae41a7d3d42e79a826811d3697528
Source dataset
uspto-grants-2015_07
Patent number
US09076665B2

Reaction notes

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