Benzenepropanoic acid, 3-(1,1-dimethylethyl)-4-hydroxy-, methyl ester → HCID 11833211, compound

HRID 430728Notes

Reaction equation

HRID 430728 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].O.[C:19](O)(=[O:22])[CH:20]=[O:21]>ClCCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([C:5]1[C:10]2[O:11][C:20](=[O:21])[CH:19]([OH:22])[C:9]=2[CH:8]=[C:7]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3084638Benzenepropanoic acid, 3-(1,1-dimethylethyl)-4-hydroxy-, methyl esterHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 11833211HCID 11833211, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

23.6 g of methyl 3-(3-tert-butyl-4-hydroxyphenyl)propionate, 10.1 g of glyoxylic acid monohydrate and 0.08 g of p-toluenesulfonic acid are boiled in 80 ml of 1,2-dichloroethane under a water separator for 7 h. The reaction solution is then cooled down, washed 3 times with 50 ml of water each time and freed of solvent in a rotary evaporator to leave 29.2 g of methyl 3-(7-tert-butyl-3-hydroxy-2-oxo-2,3-dihydrobenzofuran-5-yl)propionate in the form of a yellowish oil.

Workup

  1. temperatureThe reaction solution is then cooled down
  2. washwashed 3 times with 50 ml of water each time
  3. customfreed of solvent in a rotary evaporator

Sources & evidence

ORD record
ord-bcc761fa62b54c3aa7374e7b38900acf
Source dataset
uspto-grants-2001_11
Patent number
US06323267B1

Reaction notes

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