p-Toluenesulfonic acid → HCID 20370988, compound

HRID 616048Notes

Reaction equation

HRID 616048 reaction equation
[CH2:1]([C:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([OH:12])[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:2].[C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)[CH3:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:20][C:19]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:12][C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:4](=[O:11])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1][O:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7410AcetophenoneHCID 858062,3-Dihydroxy-1,2-diphenylpropan-1-one

Product 1

HCID 20370988HCID 20370988, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 12.1 grams (50 millimoles) of α-methylol benzoin, 6.0 grams (50 millimoles) of acetophenone, 1.0 gram of p-toluenesulfonic acid and 100 ml. of benzene was refluxed under a Dean-Stark trap for 2 hours, the mixture allowed to stand overnight at room temperature, then saturated with ammonia gas and filtered. The resulting oil was distilled at 135°-165° C at 20μ vacuum pressure to yield 10.5 grams of an only partially pure product. 7.2 grams of this product were chromatographed on silica gel with 5% diethyl ether-hexane elution to yield 6.2 grams of a product that was still not entirely pure, which was subjected to NMR and infrared examination as follows:

Workup

  1. filtrationsaturated with ammonia gas and filtered
  2. distillationThe resulting oil was distilled at 135°-165° C at 20μ vacuum pressure
  3. customto yield 10.5 grams of an only partially pure product
  4. custom7.2 grams of this product were chromatographed on silica gel with 5% diethyl ether-hexane elution

Sources & evidence

ORD record
ord-1792ff6230c845dfa973b29f697bb0dc
Source dataset
uspto-grants-1978_02
Patent number
US04072694

Reaction notes

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