Bromhydrol → 4-Hydroxy-4'-(2-methyloctanoyl) biphenyl

HRID 2372246Notes

Reaction equation

HRID 2372246 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:24])[CH:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Br-].[Al+3].[Br-].[Br-]>C1(C)C=CC=CC=1>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:24])[CH:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 166749BromhydrolHCID 19889088HCID 19889088, compound

Product 1

HCID 145974864-Hydroxy-4'-(2-methyloctanoyl) biphenylYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

Then, 400 mg (1.2 mmol) of the above 4-methoxy-4'-(2-methyloctanoyl) biphenyl was dissolved in 6 ml of dried toluene in a flask of 50 ml. After the solution was added with 1.3 g (5.0 mmol) of aluminum bromide under ice cooling for 5 minutes, the resulting mixture was stirred under ice cooling for 6 hours, at room temperature for about 60 hours and at 40° C. for 11 hours. After the completion of the reaction, the resulting product was poured into 100 ml of ice water together with 40 ml of toluene. After the separation into two layers, the organic layer was taken out, and the extraction with 40 ml of toluene on aqueous layer was repeated two times. Thereafter, the organic layers were gathered, washed with 40 ml of water and dried on anhydrous magnesium sulfate. After magnesium sulfate was filtered off, the product was concentrated and purified through a silica gel column (toluene→toluene: diethyl ether=5:1 (v/v)] to obtain 200 mg (yield: 54%) of a reddish brown oily substance of 4-hydroxy-4'-(2-methyloctanoyl) biphenyl having the following properties:

Workup

  1. customAfter the completion of the reaction
  2. customAfter the separation into two layers
  3. extractionthe extraction with 40 ml of toluene on aqueous layer
  4. washwashed with 40 ml of water
  5. dry with materialdried on anhydrous magnesium sulfate
  6. filtrationAfter magnesium sulfate was filtered off
  7. concentrationthe product was concentrated
  8. custompurified through a silica gel column (toluene→toluene

Sources & evidence

ORD record
ord-10482fbdb0584c7fac1c6f8f547d269b
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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