Benzyl 4-Hydroxybenzoate → HCID 18381591, compound

HRID 2419378Notes

Reaction equation

HRID 2419378 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:23][O:22][C:20]([CH2:19][O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1)=[O:21]

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 18381591HCID 18381591, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of benzyl 4-hydroxybenzoate (169.0g.), methyl bromoacetate (122.4g.) and anhydrous potassium carbonate (200g.) in acetone (500ml.) (analytical grade) was stirred and heated under reflux for 16 hours. The mixture was then filtered and the filtrate evaporated in vacuo. The semi-solid residue obtained was separated by filtration. The solid thus obtained was washed with cold (0°-5° C.) petroleum ether (b.p. 60°-80° C.) (50ml.) to give benzyl 4-(methoxycarbonylmethoxy)benzoate, m.p. 63°-66° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. filtrationThe mixture was then filtered
  4. customthe filtrate evaporated in vacuo
  5. customThe semi-solid residue obtained
  6. customwas separated by filtration
  7. customThe solid thus obtained
  8. washwas washed with cold (0°-5° C.) petroleum ether (b.p. 60°-80° C.) (50ml.)

Sources & evidence

ORD record
ord-fe9c123f432d45f7b73369e7e05b86ff
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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