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Phenacyl bromide → alpha-(3,4-Methylenedioxyphenoxy)acetophenone

HRID 46624
Notes
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Reaction equation

HRID 46624 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([OH:10])=[CH:4][C:3]=2[O:2]1.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([O:10][CH2:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:14])=[CH:4][C:3]=2[O:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 68289Sesamol

Product 1

HCID 20386603alpha-(3,4-Methylenedioxyphenoxy)acetophenone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 25 g. (0.181 mole) of 3,4-methylenedioxyphenol, 36 g. (0.181 mole) of α-bromoacetophenone and 41.2 g. (0.40 mole) of sodium carbonate in 350 ml. of benzene is heated to its reflux temperature and maintained at reflux for 16 hours. To the mixture is added 50 g. of potassium carbonate, and the mixture is refluxed for an additional 7 days while collecting water in a Barrett water trap. The mixture is then diluted with a mixture of water and benzene. The benzene layer is washed with water, then cold 5 percent sodium hydroxide solution. A precipitate forms in the benzene layer. It is collected, rinsed with benzene and dried to provide a white powder which is recrystallized from ethanol to provide α-(3,4-methylenedioxyphenoxy)acetophenone, m.p. 123°-126° C.

Workup

  1. additionA mixture of 25 g
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for 16 hours
  5. additionTo the mixture is added 50 g
  6. customwhile collecting water in a Barrett water trap
  7. additionThe mixture is then diluted with a mixture of water and benzene
  8. washThe benzene layer is washed with water
  9. customIt is collected
  10. washrinsed with benzene
  11. customdried
  12. customto provide a white powder which
  13. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-b0a8a49ae46944b3a2df9093aa91678e
Source dataset
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04174403

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes