Potassium Carbonate → HCID 23325177, compound

HRID 1380465Notes

Reaction equation

HRID 1380465 reaction equation
C1(C(C2[C:14]([CH2:15][O:16][CH2:17][C:18]3[C:23](C4C(=CC=C(O)C=4)O)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)=CC(=CC=1)O)O.Br[CH:33]([CH3:44])[C:34]([O:36][CH2:37][CH2:38][NH:39][C:40](=[O:43])[O:41][CH3:42])=[O:35].C(=O)([O-])[O-:46].[K+].[K+]>CC(C)=O>[CH2:17]([O:16][C:15]1[CH:10]=[CH:11][C:12]([O:46][CH:33]([CH3:44])[C:34]([O:36][CH2:37][CH2:38][NH:39][C:40](=[O:43])[O:41][CH3:42])=[O:35])=[CH:13][CH:14]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53709009HCID 53709009, compoundHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 23325177HCID 23325177, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture consisting of 2.8 g of hydroquinone monobenzyl ether, 3.56 g of methyl 2-(2-bromopropionyloxy)ethylcarbamate, 3.87 g of potassium carbonate and 30 ml of acetone is heated at reflux for 2 hours while stirring. The cooled mixture is filtered and the filtrate is evaporated. After flash chromatography, the residue gives pure methyl 2-[[2-(4-benzyloxyphenoxy)propionyl]oxy]ethylcarbamate of melting point 79°-81° C. 1.0 g thereof is dissolved in 100 ml of ethyl acetate and hydrogenated in the presence of 0.1 g of 5% palladium-on-carbon. After shaking for 45 minutes, the hydrogen uptake has finished. The catalyst is filtered off and the solvent is removed on a rotary evaporator. There is obtained methyl 2-[[2-(4-hydroxyphenoxy)propionyl]oxy]ethylcarbamate; nD20 1.5003.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe cooled mixture is filtered
  4. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-10065b89ee9648e7a7b0e81239a577c1
Source dataset
uspto-grants-1986_04
Patent number
US04582526

Reaction notes

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