Methylparaben → Methyl 4-(2,2-diethoxyethoxy)benzoate

HRID 504061Notes

Reaction equation

HRID 504061 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][CH:20]([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23]>C1COCC1>[CH2:22]([O:21][CH:20]([O:24][CH2:25][CH3:26])[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)[CH3:23]

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 10084384Methyl 4-(2,2-diethoxyethoxy)benzoateYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture containing 10 g of methyl 4-hydroxybenzoate and 22.71 g of K2CO3 in 100 ml of THF is heated at 100° C. for 5 min and cooled to room temperature, 15.54 g of 2-bromo-1,1-diethoxyethane are added and the mixture is stirred for 2 hours at room temperature and then for 32 hours at 100° C., and is allowed to return to room temperature. The inorganic material is filtered off and then rinsed with DMF. The filtrate is evaporated and then taken up in DCM, washed with water (3 times) and then with saturated NaCl solution, dried over MgSO4 and evaporated. 16.68 g of the expected compound (greater than the theoretical mass) are obtained.

Workup

  1. temperaturecooled to room temperature
  2. waitfor 32 hours at 100° C.
  3. customto return to room temperature
  4. filtrationThe inorganic material is filtered off
  5. washrinsed with DMF
  6. customThe filtrate is evaporated
  7. washwashed with water (3 times)
  8. dry with materialwith saturated NaCl solution, dried over MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-0dd55c2768c04c85bc33ae0bc218d349
Source dataset
uspto-grants-2010_08
Patent number
US07777041B2

Reaction notes

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