Hydrochloric Acid → Ethyl p-hydroxyphenyllactate

HRID 1033434Notes

Reaction equation

HRID 1033434 reaction equation
O.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([OH:14])[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.Cl.[CH2:16](OCC)[CH3:17]>C(O)C>[OH:14][CH:10]([CH2:9][C:6]1[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=1)[C:11]([O:13][CH2:16][CH3:17])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 185303102-Hydroxy-3-(4-hydroxyphenyl)propanoic acid hydrate

Product 1

HCID 21930973Ethyl p-hydroxyphenyllactate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 0.5 g (2.74 mmol) of D,L 3-(4-hydroxyphenyl) lactic acid hydrate in 10 mL of ethanol was added a catalytic amount of concentrated hydrochloric acid. The mixture was heated at reflux for 2 hours then cooled to room temperature and concentrated under vacuum. The residue was dissolved in 50 mL of ether and washed with saturated aqueous sodium bicarbonate (1×50 mL) and brine (1×50 mL). The organic layer was removed, dried over magnesium sulfate, filtered and evaporated under vacuum to afford 0.54 g (2.57 mmol,94%) of the ethyl ether. 1H NMR (200 MHz,CDCl3): 1.26 (t,7 Hz,3H), 2.86 (dd;7,14 Hz;1H); 3.03 (dd;4,14 Hz; 1H), 4.19 (q,7 Hz,2H), 4.38 (dd;4,7 Hz;1H), 5.60 (br s,1H), 6.66 (d,8 Hz,2H), 7.03 (d,8 Hz,2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in 50 mL of ether
  5. washwashed with saturated aqueous sodium bicarbonate (1×50 mL) and brine (1×50 mL)
  6. customThe organic layer was removed
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-d022ebfcde544a6db1369641f0e6dc14
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

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