Salicylic Acid → 1-(Ethoxycarbonyloxy)ethyl salicylate

HRID 1719727Notes

Reaction equation

HRID 1719727 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(N(CC)CC)C.[C:18](=[O:26])([O:23][CH2:24][CH3:25])[O:19][CH:20](Cl)[CH3:21].CCOCC>C1(C)C=CC=CC=1.O>[C:1]([O:10][CH:20]([O:19][C:18]([O:23][CH2:24][CH3:25])=[O:26])[CH3:21])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

7

Reactant 4

HCID 338Salicylic AcidHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 162095Carbonic acid, 1-chloroethyl ethyl ester

Product 1

HCID 538260801-(Ethoxycarbonyloxy)ethyl salicylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2.76 g salicylic acid, 2.02 g triethylamine and 3.5 gm 1-chloroethyl ethyl carbonate in 25 ml of toluene is refluxed for three hours. The reaction mixture is cooled and 25 ml of ether and 25 ml of water added. The organic layer is separated, washed 2× with 25 ml water, dried through sodium sulfate and concentrated in vacuo. The residue (3.88 g) is chromatographed on 200 g silica gel. Elution with 25% methylene chloride in hexane gives 1-(ethoxycarbonyloxy)ethyl salicylate which is directly used in the next step.

Workup

  1. temperatureis refluxed for three hours
  2. temperatureThe reaction mixture is cooled
  3. customThe organic layer is separated
  4. washwashed 2× with 25 ml water
  5. dry with materialdried through sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue (3.88 g) is chromatographed on 200 g silica gel
  8. washElution with 25% methylene chloride in hexane

Sources & evidence

ORD record
ord-a70b2a22e28b40d7b4e2dc80c76ead48
Source dataset
uspto-grants-1985_09
Patent number
US04542158

Reaction notes

Loading…