p-Toluidine → 2-Phenylethanol

HRID 1089034Notes

Reaction equation

HRID 1089034 reaction equation
OC1C2C(=O)C3C(=C([N+]([O-])=O)C=CC=3O)C(=O)C=2C([N+]([O-])=O)=CC=1.N[C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][OH:34])=[CH:28][CH:27]=1.NC1C=CC(C(CO)CO)=CC=1.NC1C=CC(C)=CC=1.COCCOCCO>>[CH:26]1[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][OH:34])=[CH:30][CH:31]=1

Participants

6

Reactant 5

HCID 7813p-ToluidineHCID 8134Diethylene Glycol Monomethyl EtherHCID 669044-Aminophenethyl alcoholHCID 33784401,8-Dinitro-4,5-dihydroxyanthraquinoneHCID 195939762-(4-Aminophenyl)propane-1,3-diol

Product 1

HCID 60542-Phenylethanol

Conditions

Temperature
130 °C

Procedure

A mixture of 19.4 g of 1,8-dihydroxy-4,5-dinitroanthraquinone, 25.0 g of a mixture consisting of about 72 % of 2-(4-aminophenyl)-ethanol, about 22 % of 2-(4-aminophenyl)propane-1,3-diol, about 3 % of 4-toluidine and by-products, and 140 g of diethylene glycol monomethyl ether is heated to 130° C. over a period of 2.5 hours. Stirring at 130-135° C. is continued for 6 hours, during which the water of the reaction is separated off by distillation. The reaction mixture is cooled to 100° C. and stirred into a mixture of 250 g of water, 250 g of ice and 110 g of 32 % hydrochloric acid. This crude dye suspension is filtered at about 20° C., and the product is washed with about 3 liters of water. After drying, 27 g of a dye mixture containing 65 % of the dye of the formula ##STR12## 13 % of the dye of the formula ##STR13## 3 % of the dye of the formula ##STR14## 7% of 1,8-dihydroxy-4-nitro-5-aminoanthraquinone, and 2-phenylpropane-1,3-diol and phenylethanol is obtained.

Workup

  1. customthe water of the reaction is separated off by distillation
  2. temperatureThe reaction mixture is cooled to 100° C.
  3. stirringstirred into a mixture of 250 g of water, 250 g of ice and 110 g of 32 % hydrochloric acid
  4. filtrationThis crude dye suspension is filtered at about 20° C.
  5. washthe product is washed with about 3 liters of water
  6. customAfter drying
  7. addition27 g of a dye mixture containing 65 % of the dye of the formula ##STR12## 13 % of the dye of the formula ##STR13## 3 % of the dye of the formula ##STR14## 7% of 1,8-dihydroxy-4-nitro-5-aminoanthraquinone, and 2-phenylpropane-1,3-diol

Sources & evidence

ORD record
ord-8ba5088737a041269298dfc4a45f7de2
Source dataset
uspto-grants-1990_10
Patent number
US04964876

Reaction notes

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