Potassium Carbonate → Methyl 2-[p-(benzyloxy)phenoxy]propionate

HRID 1706001Notes

Reaction equation

HRID 1706001 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]([CH3:38])[C:34]([O:36][CH3:37])=[O:35].C(=O)([O-])[O-:40].[K+].[K+]>C(C(C)=O)C>[CH2:17]([O:16][C:15]1[CH:10]=[CH:11][C:12]([O:40][CH:33]([CH3:38])[C:34]([O:36][CH3:37])=[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 95576Methyl 2-bromopropionateHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 13093988Methyl 2-[p-(benzyloxy)phenoxy]propionateYield 197.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 60 g of hydroquinone monobenzyl ether, 50 g of methyl 2-bromopropionate, 42 g of anhydrous potassium carbonate and 500 ml of methyl ethyl ketone, is heated with stirring for 24 hours to reflux temperature. After it has cooled, the reaction mixture is filtered and washed with methyl ethyl ketone. The filtrate is then concentrated in vacuo. The residual oil soon becomes crystalline. Recrystallisation from cyclohexane/petroleum ether yields 82 g of methyl 4-(benzyloxy)-α-phenoxypropionate with a melting point of 67°-68° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature
  3. temperatureAfter it has cooled
  4. filtrationthe reaction mixture is filtered
  5. washwashed with methyl ethyl ketone
  6. concentrationThe filtrate is then concentrated in vacuo
  7. customRecrystallisation from cyclohexane/petroleum ether

Sources & evidence

ORD record
ord-9d57615da9a64ffb813c9bfaff1061df
Source dataset
uspto-grants-1980_06
Patent number
US04205978

Reaction notes

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