3,4-Dimethoxyphenethyl alcohol → Methyl 2-hydroxy-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-di(4-ethylphenyl)propionate

HRID 433930Notes

Reaction equation

HRID 433930 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=3)[O:15][CH:10]2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)[CH3:2].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:34][CH2:35][OH:36])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]>ClCCl.B(F)(F)F.CCOCC>[OH:15][CH:10]([C:9]([O:36][CH2:35][CH2:34][C:28]1[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=1)([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=1)[C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 819113,4-Dimethoxyphenethyl alcoholHCID 18756192Methyl 3,3-di(4-ethylphenyl)-2,3-epoxypropionate

Product 1

HCID 10743745Methyl 2-hydroxy-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-di(4-ethylphenyl)propionate

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 6344DichloromethaneSolvent

Procedure

6 g (19.3 mmol) of methyl 3,3-di(4-ethylphenyl)-2,3-epoxypropionate (crude) and 3.52 g (19.3 mmol) of 2-(3,4-dimethoxyphenyl)ethanol were dissolved in 20 ml of dichloromethane and, at room temperature, 5 drops of boron trifluoride etherate were added. The solution was stirred for 1.5 hours. The solvent was then distilled off, and the residue, a pale yellow oil (8.66 g, 91%), was immediately reacted further.

Workup

  1. distillationThe solvent was then distilled off
  2. customthe residue, a pale yellow oil (8.66 g, 91%), was immediately reacted further

Sources & evidence

ORD record
ord-9ce4b38f49c04a2398f2a9f84b815cc3
Source dataset
uspto-grants-2003_12
Patent number
US06670367B1

Reaction notes

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