Ammonia → HCID 10978526, compound

HRID 725408Notes

Reaction equation

HRID 725408 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:25])[CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:11][C:10]=1[O:26][CH3:27])C1C=CC=CC=1.N.CCCCCC>Br.C(O)(=O)C.CCOCC>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:25])[CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:11][C:10]=1[O:26][CH3:27]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 8058HexaneHCID 11068396HCID 11068396, compound

Product 1

HCID 10978526HCID 10978526, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.0 g of 4'-(benzyloxy)-3'-methoxy-4-phenylbutyrophenone in 40 ml of 33 percent hydrobromic acid in glacial acetic acid is stirred at room temperature for 5 hours and subsequently poured into 500 ml of ice-water. The solution is adjusted to pH 6.0 by the addition of conc. ammonia and extracted three times with 250 ml of ethyl acetate each time. The organic phase is washed three times with 50 ml of water each time, dried over sodium sulfate and evaporated. The oil obtained is dissolved in 20 ml of ether, whereupon the solution is treated with hexane until it becomes turbid and is left to crystallize out. There is obtained colorless 4'-hydroxy-3'-methoxy-4-phenylbutyrophenone of m.p. 91°-92°.

Workup

  1. extractionextracted three times with 250 ml of ethyl acetate each time
  2. washThe organic phase is washed three times with 50 ml of water each time
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe oil obtained
  6. waitis left
  7. customto crystallize out

Sources & evidence

ORD record
ord-159a407992354dcbaca3c02c2895ee33
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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