Bromide ion → HCID 19023816, compound

HRID 2165479Notes

Reaction equation

HRID 2165479 reaction equation
[Br-].[CH:2](=[O:10])[C:3]1[C:4](=[CH:6][CH:7]=[CH:8][CH:9]=1)[OH:5].C(=O)([O-])[O-].[K+].[K+].[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CN(C)C=O>[C:19]1([CH2:6][CH2:4][CH2:3][CH2:9][CH2:8][CH2:7][O:5][C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[CH:2]=[O:10])[CH:18]=[CH:17][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 6998SalicylaldehydeHCID 8058HexaneHCID 11430Potassium Carbonate

Product 1

HCID 19023816HCID 19023816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 6-phenylhexanoic acid (19.8 mmoles) in sieve dried tetrahydrofuran (5 ml) was reduced with diborane in tetrahydrofuran (30 ml, 29.1 mmoles) at 0° C. for 4 hours to give 6-phenylhexanol. To an ice cold solution of the hexanol (ca. 19.8 mmoles) and carbon tetrabromide (21.98 mmoles) in methylene chloride (50 ml) was added triphenylphosphine (22.30 mmoles) in methylene chloride (50 ml) and the resulting solution was stirred for 2.5 hours. The volatiles were evaporated and the residue was taken up in ether (100 ml), cooled in ice, and filtered. The filtrate was evaporated and distilled to afford 6-phenylhexyl bromide as an oil. A mixture of the bromide (8.00 mmoles), salicylaldehyde (8.19 mmoles) and potassium carbonate (9.33 mmoles) in dimethylformamide (10 ml) was heated to 100° C. and maintained at that temperature for one hour. The cooled reaction mixture was taken up in hexane (50 ml) and washed with 5% sodium hydroxide (50 ml) and saturated sodium chloride (50 ml). The organic phase was dried over anhydrous magnesium sulfate and charcoal. Evaporation yielded a colorless oil which was purified by flash chromatography over silica gel with 5% ethyl acetate in hexane as eluant to afford the desired product as an oil.

Workup

  1. temperaturemaintained at that temperature for one hour
  2. customThe cooled reaction mixture
  3. washwashed with 5% sodium hydroxide (50 ml) and saturated sodium chloride (50 ml)
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate and charcoal
  5. customEvaporation
  6. customyielded a colorless oil which
  7. customwas purified by flash chromatography over silica gel with 5% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-efa37a4c52a74504a7a4f041eb0436d2
Source dataset
uspto-grants-1990_07
Patent number
US04939279

Reaction notes

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