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

HRID 1701463Notes

Reaction equation

HRID 1701463 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. Recrystallization 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. customRecrystallization from cyclohexane/petroleum ether

Sources & evidence

ORD record
ord-7fe27892c690438c9c3f7bc59c5d2302
Source dataset
uspto-grants-1980_03
Patent number
US04193790

Reaction notes

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