Phenol → HCID 19979676, compound

HRID 1461889Notes

Reaction equation

HRID 1461889 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:17]1(O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C)C=O.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH2:13][C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 54637793-(3-tert-Butyl-4-hydroxyphenyl)propanoic acid

Product 1

HCID 19979676HCID 19979676, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of 55 g of 3-(3-tert-butyl-4-hydroxyphenyl)-propionic acid, 35 g of phenol, 7 g of dimethylformamide, 19.1 g of phosphorus oxychloride and 250 ml of toluene was stirred at 70° C. for 6 hours. The mixture was cooled to room temperature, and 800 ml of toluene was added thereto. The mixture was washed with water and an aqueous solution of sodium hydroxide, followed by washing with water. The mixture was concentrated, and the residue was purified by silica gel column chromatography to give 66.5 g of phenyl 3-(3-tert-butyl-4-hydroxyphenyl)propionate as a white crystal, m.p. 106°-109° C.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washThe mixture was washed with water
  3. washby washing with water
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-319b8e45869d424aae9fc361fef4f873
Source dataset
uspto-grants-1991_12
Patent number
US05077424

Reaction notes

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