Water → Triphenylcarbinol

HRID 978967Notes

Reaction equation

HRID 978967 reaction equation
N1C=CC=CC=1.C([O:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)C(C)=C.O>C1COCC1>[C:14]1([C:13]([OH:12])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 12641353Triphenylmethyl 2-methylprop-2-enoate

Product 1

HCID 6457Triphenylcarbinol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure of Example 2 was repeated except that 3.96 g (0.05 mol) of dry pyridine was used in place of triethylamine and the reaction was carried out in THF. It was confirmed when the reaction solution was examined by means of thin-layer chromatography that triphenylmethyl methacrylate was quantitatively formed. After the amine salt was removed by filtration, the solvent and excess pyridine were evaporated. The intended product was obtained as a syrup. An attempt to recrystallize it from ether and n-hexane failed, since hydrolysis took place due to water contained in the solvents for recrystallization and triphenylmethyl alcohol was formed.

Workup

  1. customwas quantitatively formed
  2. customAfter the amine salt was removed by filtration
  3. customthe solvent and excess pyridine were evaporated
  4. customThe intended product was obtained as a syrup
  5. customAn attempt to recrystallize it from ether and n-hexane
  6. customfailed, since hydrolysis
  7. customcontained in the solvents for recrystallization

Sources & evidence

ORD record
ord-a14cc1244ab845b09a26a6d7298f3efc
Source dataset
uspto-grants-1987_05
Patent number
US04666633

Reaction notes

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