Butyl bromide → HCID 21997463, compound

HRID 1977282Notes

Reaction equation

HRID 1977282 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:18](Br)[CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 10340Sodium CarbonateHCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate

Product 1

HCID 21997463HCID 21997463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-(4′-hydroxyphenyl)benzoate (2.02 g), n-butylbromide (3 ml) and sodium carbonate (3.6 g) in N,N-dimethylformamide was stirred for 17 hours at 80° C. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine. After dried over magnesium sulfate, the solution was evaporated in vacuo. The residue was triturated with n-hexane to afford methyl 4-(4′-butyloxyphenyl)benzoate (2.45 g).

Workup

  1. custompartitioned between ethyl acetate and water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialAfter dried over magnesium sulfate
  5. customthe solution was evaporated in vacuo
  6. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-16c1101b54694423ae2b4b3313841cc5
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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