Paraldehyde → HCID 21614688, compound

HRID 616046Notes

Reaction equation

HRID 616046 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].[CH3:19][CH:20]1OC(C)OC(C)O1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[CH3:19][CH:20]1[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 2

HCID 31264ParaldehydeHCID 858062,3-Dihydroxy-1,2-diphenylpropan-1-one

Product 1

HCID 21614688HCID 21614688, compoundYield 107.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 10.0 grams (41 millimoles)αmethylol benzoin, 20.0 grams (45 millimoles) paraldehyde, 0.5 grams p-toluenesulfonic acid and 100 ml. benzene was heated with magnetic stirring to 80°-90° C for 30 minutes under a Dean-Stark trap under conditions such that refluxing occurred, but the vapors condensed before reaching the trap. The temperature of the reaction mixture was then gradually raised to 120°-130° C and 8 ml. water was collected. The reaction mixture was then saturated with ammonia gas, the resulting salt precipitate removed by filtration on a Buchner funnel to provide a benzene solution of the reaction product. The benzene solvent was removed under vacuum. A yield of 11.8 grams of a yellow oil was obtained. The yellow oil was chromatographed on silica gel with 5% ethyl ether in n-hexane elution to provide 9.5 grams of an odorous yellow oil which distilled at 125°-130° C at 20μ vacuum pressure to provide 6.5 grams of a light yellow oil product.

Workup

  1. temperaturethat refluxing
  2. customthe vapors condensed
  3. temperatureThe temperature of the reaction mixture was then gradually raised to 120°-130° C
  4. customwater was collected
  5. customsaturated with ammonia gas, the resulting salt precipitate removed by filtration on a Buchner funnel
  6. customto provide a benzene solution of the reaction product
  7. customThe benzene solvent was removed under vacuum

Sources & evidence

ORD record
ord-432bb6dcc7a5425d8e9a07033a9e36e4
Source dataset
uspto-grants-1978_02
Patent number
US04072694

Reaction notes

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