Water → HCID 53916505, compound

HRID 2289871Notes

Reaction equation

HRID 2289871 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[CH2:23][CH2:24][CH:25]([C:27]1[C:32]([CH3:33])=[C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]([CH3:42])=[C:29]([CH3:43])[C:28]=1[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.CCCCCC.C(OC(=O)C)C>C1C=CC=CC=1>[CH2:45]([O:44][C:28]1[C:29]([CH3:43])=[C:30]([CH3:42])[C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:32]([CH3:33])[C:27]=1[CH:25]=[CH:24][CH2:23][C:10]1[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 10996014HCID 10996014, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 53916505HCID 53916505, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.39 g(3.46 mmol) of 3-(2,4-dibenzyloxy-phenyl)-1-(2,5-dibenzyloxy-3,4,6-trimethyl-phenyl)-propan-1-ol was diluted with 100 ml of dry benzene and 30 mg of p-toluenesulfonic acid was added thereto. The mixture was stirred for 4 hours while refluxing to eliminate water. The solution thus produced was cooled down to room temperature and washed once(×1) with saturated aqueous sodium hydrogen carbonate solution. The washings was extracted with dichloromethane and the extract was combined with the original organic layer. Then, the combined mixture was dried, distilled under reduced pressure and subjected to a silica gel column chromatography(eluent: n-hexane/ethylacetate=10/1, v/v) to obtain 2.1 g(Yield 90%) of 4-[3-(2,5-dibenzyloxy-3,4,6-trimethylphenyl)-allyl]-1,3-dibenzyloxy-benzene. 2.1 g(3.12 mmol) of the compound thus obtained was diluted with 30 ml of ethylacetate, to which was slowly added 45 mg of 10% palladium catalyst. The resulting solution was stirred for 72 hours under hydrogen atmosphere of 60 psi, diluted with 50 ml of ethylacetate and then filtered. The filtrate was distilled under reduced pressure and subjected to a silical gel column chromatography(eluent: n-hexane/ethylacetate=1/1, v/v) to obtain 0.74 g (Yield 79%) of the title compound.

Workup

  1. additionwas added
  2. temperaturewhile refluxing
  3. customThe solution thus produced
  4. washwashed once(×1) with saturated aqueous sodium hydrogen carbonate solution
  5. extractionThe washings was extracted with dichloromethane
  6. customThen, the combined mixture was dried
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-10559116db014225935a435983e4abc5
Source dataset
uspto-grants-2000_07
Patent number
US06093836

Reaction notes

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