Benzyl Bromide → HCID 10662890, compound

HRID 2253734Notes

Reaction equation

HRID 2253734 reaction equation
[C:1]([CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11](=[O:16])[CH:10]=[CH:9]2)([O:3]C)=[O:2].[OH-:17].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C.O>[C:11](/[CH:10]=[CH:9]\[C:8]1[CH:7]=[C:6]([CH2:5][C:1]([OH:3])=[O:2])[CH:15]=[CH:14][C:13]=1[O:12][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([OH:16])=[O:17]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 10608836HCID 10608836, compound

Product 1

HCID 10662890HCID 10662890, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2.63 g (12.06 mmoles) of 6-carbomethoxymethylcoumarin in 50 ml of ethanol is added 2.41 g (60.30 mmoles) of NaOH in 3 ml of H2O. The reaction mixture is heated to reflux for 8 hours after which time 40 ml (3.36 moles) of benzylbromide is added. The reaction mixture is stirred at room temperature for 12 hours after which time the reaction mixture is concentrated in vacuo. The crude product is taken up in H2O, washed with ethylacetate (2 times) and acidified to pH 3-4 with concentrated HCl. The resulting white precipitate is collected to yield cis-3-carboxyvinyl-4-benzyloxyphenylacetic acid which is used directly in the next step.

Workup

  1. temperatureThe reaction mixture is heated
  2. additionis added
  3. concentrationis concentrated in vacuo
  4. washwashed with ethylacetate (2 times)
  5. customThe resulting white precipitate is collected

Sources & evidence

ORD record
ord-bd7e4e83f6a04121b1ae94dce0f676d5
Source dataset
uspto-grants-1993_08
Patent number
US05232948

Reaction notes

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