Hydrochloric Acid → 3-Pentanone, 1,5-bis(4-hydroxyphenyl)-

HRID 1378397Notes

Reaction equation

HRID 1378397 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](=[O:22])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[Br-].[Br-].[Br-].[Al+3].Cl.C(OCC)C>C1(C)C=CC=CC=1>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](=[O:22])[CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 166749BromhydrolHCID 2801509HCID 2801509, compound

Product 1

HCID 107071713-Pentanone, 1,5-bis(4-hydroxyphenyl)-Yield 105.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1,5-bis(4-methoxyphenyl)-3-pentanone (2.1 g, 7 mmol), prepared as in step 1, and aluminum tribromide (10.64 g, 40 mmol) in toluene (60 mL) was refluxed at 80° C. for 30 minutes and then cooled to room temperature. The reaction mixture was slowly added to a mixture of aqueous 1N HCl (150 mL) and ethyl ether (150 mL). The ether layer was separated, washed with aqueous 1N HCl, water, and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide 1,5-bis-(4-hydroxyphenyl)-3-pentanone (2 g).

Workup

  1. temperaturecooled to room temperature
  2. customThe ether layer was separated
  3. washwashed with aqueous 1N HCl, water, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e64b37853f624052aa2812074ec6410c
Source dataset
uspto-grants-1997_09
Patent number
US05668146

Reaction notes

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