Benzene → Ethyl 3,3-dibenzyloxypropionate

HRID 1647543Notes

Reaction equation

HRID 1647543 reaction equation
[CH2:1]([O:3][CH:4]([O:11][CH2:12][CH3:13])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17]C=1.[CH:22]1[CH:27]=[CH:26]C=[CH:24][CH:23]=1>CCOCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:12]([O:11][CH:4]([O:3][CH2:1][C:2]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:15]=1)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:13]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 241BenzeneHCID 244Benzyl AlcoholHCID 66389Ethyl 3,3-diethoxypropionate

Product 1

HCID 14825901Ethyl 3,3-dibenzyloxypropionateYield 99.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a 1000 mL round-bottomed flask was added ethyl 3,3-diethoxypropionate (20.0 g, 0.1051 mole), benzyl alcohol (22.7 g, 0.2102 mole), p-toluenesulfonic acid monohydrate (0.5 g, 0.0026 mole) and benzene (800 mL). The reaction can also be carried out in hexanes Heating the mixture at 80° C., the solvent was distilled from the reaction mixture in a 3.5 hour period monitored by 300 MHz NMR. The reaction can be carried out in hexanes. The resulting residue was dissolved in ether (@300 mL) and washed with saturated sodium bicarbonate solution (100 mL) and brine (100 mL). The organic layer was dried over anhydrous magnesium sulfate and the solvent removed in vacuo to give ethyl 3,3-dibenzyloxypropionate (9) as a colorless oil (32.9 g, 99.5% yield): 1H NMR (CDCl3) d 1.22 (t, 3H, J=7.2 Hz), 2.79 (d, 2H, J =5.9 Hz), 4.12 (q, 2H, J=7.2 Hz), 4.60 (d, 2H, J=11.6 Hz), 4.70 (d, 2H, J=11.6 Hz), 5.22 (t, 1H, J=6 Hz), 7.27-7.36 (m, 10H); IR (Neat) 3100, 3080, 3040, 2990, 2940, 2920, 2885, 1740, 1630, 1458, 1375, 1315, 1190, 1120, 1050, 1030, 740, 700. ##STR10##

Workup

  1. customThe reaction
  2. customat 80° C.
  3. distillationthe solvent was distilled from the reaction mixture in a 3.5 hour period
  4. customThe reaction
  5. washwashed with saturated sodium bicarbonate solution (100 mL) and brine (100 mL)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e92c6f93bddd4de6ad0f760afbd1deae
Source dataset
uspto-grants-1995_07
Patent number
US05432273

Reaction notes

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