Benzene → HCID 21552114, compound

HRID 268439Notes

Reaction equation

HRID 268439 reaction equation
COC1C=C([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH2:20][CH3:21])[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=2)=[O:11])C=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:32]1([OH:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[CH:39]1C=CC=CC=1>>[OH:18][C:15]1[CH:14]=[CH:13][C:12]([C:10](=[O:11])[CH:9]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:20][CH2:21][C:34]2[CH:35]=[CH:36][CH:37]=[C:32]([O:38][CH3:39])[CH:33]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 996PhenolHCID 6451240Aluminum(III) ChlorideHCID 86733189HCID 86733189, compound

Product 1

HCID 21552114HCID 21552114, compound

Procedure

A mixture of 11.65 g. of 4-(m-methoxyphenyl-1-(p-methoxyphenyl)-2-phenyl-1-butanone and 13.6 g. of aluminum chloride in 270 ml. of benzene was heated at reflux for 31/2 hours. The solution was allowed to cool and washed in turn with 2.5 N hydroxhloric acid, water and a saturated solution of sodium chloride. The organic layer was then extracted with 5 portions of 110 ml. each of N sodium hydroxide. Acidification of this last extract gave 11.04 g. of the crude phenol. A single recrystallization from aqueous methanol afforded 8.42 g. of 1(p-hydroxyphenyl)-4-(m-methoxyphenyl)-2-phenyl-1-butanone, m.p. 125°-129° C. (yield, 75%)

Workup

  1. additionA mixture of 11.65 g
  2. temperatureat reflux for 31/2 hours
  3. temperatureto cool
  4. washwashed in turn with 2.5 N hydroxhloric acid, water
  5. extractionThe organic layer was then extracted with 5 portions of 110 ml
  6. extractionAcidification of this last extract
  7. customgave 11.04 g
  8. customA single recrystallization from aqueous methanol
  9. customafforded 8.42 g

Sources & evidence

ORD record
ord-e64bba4c4bf9412f85eb8aa11b2540fb
Source dataset
uspto-grants-1976_03
Patent number
US03947520

Reaction notes

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