Methylparaben → HCID 68464923, compound

HRID 1785625Notes

Reaction equation

HRID 1785625 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1>CN(C=O)C>[O:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH:22]1[O:21][CH2:20][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 68464923HCID 68464923, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture containing 40 g of methyl 4-hydroxybenzoate and 90.84 g of K2CO3 in 400 ml of DMF is heated to 100° C. and 71.47 g of 2-(2-bromoethoxy)tetrahydro-2H-pyran are added slowly, with continued heating for 8 hours. The inorganic material is filtered off and rinsed with DMF. The filtrate is evaporated under vacuum and then taken up in DCM, washed 3 times with water, dried over MgSO4 and then evaporated. 77.66 g of the expected compound are obtained.

Workup

  1. temperaturewith continued heating for 8 hours
  2. filtrationThe inorganic material is filtered off
  3. washrinsed with DMF
  4. customThe filtrate is evaporated under vacuum
  5. washwashed 3 times with water
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-a21cda3d25f44f7885ea0a6d5dc02417
Source dataset
uspto-grants-2009_03
Patent number
US07504511B2

Reaction notes

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