Water → HCID 12094374, compound

HRID 2186274Notes

Reaction equation

HRID 2186274 reaction equation
[C:1]([C:5]1[C:6]([OH:21])=[CH:7][C:8]([CH:12]([CH:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)O)=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(Cl)(Cl)Cl>[C:1]([C:5]1[C:6]([OH:21])=[CH:7][C:8]2[CH2:12][C:14]3([O:11][C:9]=2[CH:10]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 23442891HCID 23442891, compound

Product 1

HCID 12094374HCID 12094374, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 0.66 g of 5-t-butyl-2-(cycloheptylhydroxymethyl)benzene-1,4-diol dissolved in 20 ml of chloroform was added 0.44 g of p-toluenesulfonic acid monohydrate and the mixture was stirred at room temperature for a whole day and night. After the reaction mixture was poured into water and extracted with chloroform, the organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate) to give 0.27 g of 6-t-butyl-5-hydroxy-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane as a white solid (yield 43%).

Workup

  1. extractionextracted with chloroform
  2. washthe organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate)

Sources & evidence

ORD record
ord-74c11bb88a09457ea2447ee11650dff3
Source dataset
uspto-grants-2002_06
Patent number
US06403639B1

Reaction notes

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