p-Toluenesulfonic acid → HCID 70452876, compound

HRID 1731792Notes

Reaction equation

HRID 1731792 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH:27]([CH3:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:26])=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([CH:27]([CH3:34])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:26])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 467833091-(4-Hydroxyphenyl)-2-phenylpropan-1-one

Product 1

HCID 70452876HCID 70452876, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2,3-Dihydropyran (4.6 g.) and a few crystals of toluene-p-sulphonic acid were added to a solution of 4-hydroxy-α-methyldesoxybenzoin (11.3 g.) in chloroform (100 ml.). The resulting solution was heated under reflux for 5 mins., cooled and washed with 5% w/v aqueous sodium bicarbonate solution. The chloroform solution was then dried and evaporated, and the residue crystallised from acetone to give 4-(2-tetrahydropyranyloxy)-α-methyldesoxybenzoin (5.93 g.), m.p. 94°-96° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 5 mins
  3. temperature, cooled
  4. washwashed with 5% w/v aqueous sodium bicarbonate solution
  5. dry with materialThe chloroform solution was then dried
  6. customevaporated
  7. customthe residue crystallised from acetone

Sources & evidence

ORD record
ord-e7c676f88cfc436f9ba42c76493eb1b0
Source dataset
uspto-grants-1986_11
Patent number
US04623660

Reaction notes

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