Benzyl Bromide → HCID 18522258, compound

HRID 342073Notes

Reaction equation

HRID 342073 reaction equation
[CH2:1]([C:4]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:2]=[CH2:3].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:1]([C:4]1[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11805862HCID 11805862, compound

Product 1

HCID 18522258HCID 18522258, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 2-allyl-3-hydroxybenzoate (20.6 g, 100 mmol), benzyl bromide (18 g, 105 mmol), and potassium carbonate (17 g, 123 mmol), was heated in DMF to 100° C. for 18 hr. The mixture was cooled and diluted with water (500 ml), and extracted with ethyl acetate three times. The ethyl acetate extracts were dried over brine and concentrated in vacuo to a tan oil (29.6 g, 100%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe ethyl acetate extracts were dried over brine
  4. concentrationconcentrated in vacuo to a tan oil (29.6 g, 100%)

Sources & evidence

ORD record
ord-e21a4cad4d3c47ba8adc4a0b80f53106
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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