Ethylparaben → HCID 86745266, compound

HRID 1460202Notes

Reaction equation

HRID 1460202 reaction equation
Cl[CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1.[OH:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1.[C:28](=[O:31])([O-:30])[O-].[K+].[K+]>CN(C)C=O>[C:21]([OH:23])(=[O:22])/[CH:20]=[CH:19]/[C:28]([OH:30])=[O:31].[C:10]1([CH2:9][N:5]2[CH2:6][CH2:7][O:8][CH:3]([CH2:2][O:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=3)[CH2:4]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 28015624-Benzyl-2-(chloromethyl)morpholine

Product 1

HCID 86745266HCID 86745266, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 11.3 parts of 2-chloromethyl-4-(phenylmethyl)morpholine (described in Synth. Comm. 1980, 10(1), 59-73), 8.3 parts of ethyl 4-hydroxybenzoate, 6.9 parts of potassium carbonate and 141 parts of N,N-dimethylformamide was stirred overnight at 110° C. The reaction mixture was evaporated and water was added to the residue. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was converted into the (E)-2-butenedioate salt in 2-propanol, yielding 9.5 parts (40.3%) of ethyl 4-[[4-(phenylmethyl)-2-morpholinyl]methoxy]benzoate (E)-2-butenedioate(1:1); mp. 174.4° C. (interm. 1).

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater was added to the residue
  3. extractionThe product was extracted with dichloromethane
  4. customthe extract was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-515c5514879f4dc2b4cb9838c06f19e6
Source dataset
uspto-grants-1991_12
Patent number
US05070090

Reaction notes

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