Water → 4-Ethenylphenyl acetate

HRID 248582Notes

Reaction equation

HRID 248582 reaction equation
O.C(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=1)(=O)C.C(OC(=O)C)(=O)C.P(=O)(O)(O)O>C(O)(=O)C>[C:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([CH:7]=[CH2:6])=[CH:9][CH:10]=1)(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 1004Phosphoric Acid2×HCID 7918Acetic AnhydrideHCID 111954024-(2-Acetoxy-ethyl)phenyl Acetate

Product 1

HCID 758214-Ethenylphenyl acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A flask heated by hot oil was fitted with a chilled water overhead condenser, a thermowell with a thermocouple, an overhead stirrer and a vacuum pump. Crude APMC-Ether (20 grams) containing 78.2 weight percent APMC-Ether, 7.2 weight percent APMC and 3.9 weight percent 4-acetoxyphenylmethylcarbinol acetate (sometimes referred to herein as "APMC-Acetate") was mixed in another flask with six (6.0) grams of acetic anhydride. Phosphoric acid (0.022 grams) having a concentration of 85 weight percent that corresponds to 0.32 moles of pure phosphoric acid per 100 moles of APMC-Ether was added to said mixture. The resultant mixture was fed to the hot flask at a rate of 1.2 grams per minute. The hot oil temperature was maintained at about 220° C. to about 230° C. and the reaction mass temperature in the hot flask was maintained at about 180° C. to about 200° C. The vacuum pump maintained a vacuum in the flask at about 80 mm Hg. 4-acetoxystyrene and acetic acid were produced in the hot flask.

Workup

  1. temperatureA flask heated by hot oil
  2. additionwas added
  3. temperatureThe hot oil temperature was maintained at about 220° C. to about 230° C.
  4. temperaturethe reaction mass temperature in the hot flask was maintained at about 180° C. to about 200° C
  5. temperatureThe vacuum pump maintained a vacuum in the flask at about 80 mm Hg

Sources & evidence

ORD record
ord-14312ca10d074038b708283d34a8e10b
Source dataset
uspto-grants-1993_05
Patent number
US05210278

Reaction notes

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