p-Toluenesulfonic acid → 4-(Hex-1-en-1-yl)benzene-1,2-diol

HRID 569642Notes

Reaction equation

HRID 569642 reaction equation
O1CCCCC1[O:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:11]=[CH:12][C:13]=1[O:14]C1CCCCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(N(CC)CC)C>[OH:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:11]=[CH:12][C:13]=1[OH:14]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54203799HCID 54203799, compound

Product 1

HCID 534261164-(Hex-1-en-1-yl)benzene-1,2-diolYield 57.8%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 887MethanolSolvent

Procedure

In 10 ml of absolute methanol was dissolved 198 mg of 1-(3',4'-bistetrahydropyranyloxy-phenyl)-1-hexene obtained in Example 17-(1), and a catalytic amount of p-toluenesulfonic acid was added to the solution at 0° C. The mixture was stirred for 2 hours at the same temperature. After reaction, one drop of triethylamine was added to the reaction mixture and the mixture was concentrated to give crude product. By purification of the crude product by means of column chromatography [silica gel/ether:hexane (1:2)], 61 mg of pure product was obtained.

Workup

  1. additionwas added to the reaction mixture
  2. concentrationthe mixture was concentrated
  3. customto give crude product
  4. customBy purification of the crude product by means of column chromatography [silica gel/ether:hexane (1:2)]

Sources & evidence

ORD record
ord-ed314e311b6049a7876f87f064a54632
Source dataset
uspto-grants-1988_03
Patent number
US04733002

Reaction notes

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