Sodium Carbonate → N-(2-methylbenzyloxycarbonyl)-tyrosinol

HRID 1439002Notes

Reaction equation

HRID 1439002 reaction equation
[NH2:1][C@H:2]([CH2:11][OH:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:13][C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[CH2:16][O:17][C:18](Cl)=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C>[CH3:13][C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[CH2:16][O:17][C:18]([NH:1][C@H:2]([CH2:11][OH:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)=[O:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 151247TyrosinolHCID 132929302-Methylbenzyloxycarbonyl chloride

Product 1

HCID 53904979N-(2-methylbenzyloxycarbonyl)-tyrosinolYield 72.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixture of 10 ml of water and 20 ml of ethyl acetate, 1.6 g of tyrosinol was dissolved. To the solution were added dropwise 2 g of 2-methylbenzyloxycarbonyl choride and 10 ml of an aqueous solution containing 1.3 g of sodium carbonate alternately with stirring while cooling with ice. After stirring for two hours at room temperature, the ethyl acetate layer was collected and washed with 5% hydrochloric acid and then with water. The layer was dried and concentrated to dryness. The residue was crystallized from ethyl acetate-petroleum ether to give 2.2 g of N-(2-methylbenzyloxycarbonyl)-tyrosinol with a mp. 78°-81° C in a yield of 70%. Analysis, calculated for C18H21O4N C 68.55, H 6.72. N 4.44, found C 68.88, H 6.84, N 4.42. According to the same procedure as used in Example 38, the following tyrosinol derivatives were prepared from the corresponding chlorides.

Workup

  1. dissolutionwas dissolved
  2. temperaturewhile cooling with ice
  3. stirringAfter stirring for two hours at room temperature
  4. customthe ethyl acetate layer was collected
  5. washwashed with 5% hydrochloric acid
  6. customThe layer was dried
  7. concentrationconcentrated to dryness
  8. customThe residue was crystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-4ed3c5e4fae24729bb4aa53a55a133ce
Source dataset
uspto-grants-1977_11
Patent number
US04057629

Reaction notes

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