O-Xylene → HCID 54243444, compound

HRID 2163405Notes

Reaction equation

HRID 2163405 reaction equation
[C:1]([C:4]1[C:31]([OH:32])=[CH:30][CH:29]=[CH:28][C:5]=1[O:6][CH2:7][CH:8]([OH:27])[CH2:9][O:10][C:11]1[C:16]2[C:17](=[O:26])[CH:18]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[O:20][C:15]=2[CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2].[CH3:33][N:34]([CH:36](OC)OC)[CH3:35].C1(C)C(C)=CC=CC=1>CO>[CH3:33][N:34]([CH3:36])[CH:35]=[CH:2][C:1]([C:4]1[C:31]([OH:32])=[CH:30][CH:29]=[CH:28][C:5]=1[O:6][CH2:7][CH:8]([OH:27])[CH2:9][O:10][C:11]1[C:16]2[C:17](=[O:26])[CH:18]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[O:20][C:15]=2[CH:14]=[CH:13][CH:12]=1)=[O:3]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 78373Dimethylformamide dimethyl acetalHCID 13090971HCID 13090971, compound

Product 1

HCID 54243444HCID 54243444, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.884 parts of ethyl 5-(3-[2-acetyl-3-hydroxyphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylate and 0.235 parts of N,N-dimethylformamidedimethylacetal was stirred in 43 parts of xylene at 120°-130° for 3 hours whilst the methanol produced was removed simultaneously by fractional distillation. Overnight cooling of the resulting solution gave a solid which was collected and crystallised from ethanol to give 0.3362 parts of ethyl 5-(3-[2-{3-dimethylaminoacryloyl}-3-hydroxyphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylate, m.pt. 159°-165°.

Workup

  1. customproduced
  2. customwas removed simultaneously by fractional distillation
  3. temperatureOvernight cooling of the resulting solution
  4. customgave a solid which
  5. customwas collected
  6. customcrystallised from ethanol

Sources & evidence

ORD record
ord-c12e07cd242c481e9ae8fbc6baf3b100
Source dataset
uspto-grants-1979_01
Patent number
US04133889

Reaction notes

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