Ethyl 3-hydroxy-3-(4-methoxyphenyl)-2-methylpropanoate → Ethyl 3-(4-methoxyphenyl)-2-methylprop-2-enoate

HRID 461095Notes

Reaction equation

HRID 461095 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9](O)[CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.S([O-])(O)(=O)=O.[K+]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 312882Ethyl 3-hydroxy-3-(4-methoxyphenyl)-2-methylpropanoateHCID 516920Potassium bisulfate

Product 1

HCID 53711494Ethyl 3-(4-methoxyphenyl)-2-methylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 71.8 g (0.30 mole) of ethyl β-(p-methoxyphenyl)-β-hydroxy-α-methylpropionate is refluxed with 41.0 g (0.30 mole) of potassium hydrogen sulfate in 718 ml of benzene for 1 hour. The insoluble white crystals formed are filtered off, washed with benzene and the solvent of the filtrate is removed on evaporation. This is dissolved in 700 ml of ether. The ether solution is washed with 4 × 100 ml of cold water until neutral followed by 80 ml of saturated sodium chloride solution, then it is dried over magnesium sulfate for 1.5 hours and filtered. The solvent is removed on an evaporator to give ethyl p-methoxy-α-methylcinnamate.

Workup

  1. customThe insoluble white crystals formed
  2. filtrationare filtered off
  3. washwashed with benzene
  4. customthe solvent of the filtrate is removed on evaporation
  5. dissolutionThis is dissolved in 700 ml of ether
  6. washThe ether solution is washed with 4 × 100 ml of cold water
  7. dry with materialit is dried over magnesium sulfate for 1.5 hours
  8. filtrationfiltered
  9. customThe solvent is removed on an evaporator

Sources & evidence

ORD record
ord-39daad5a7252463c95e3a8965db6eb2c
Source dataset
uspto-grants-1977_12
Patent number
US04061771

Reaction notes

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