Dimethylformamide → HCID 86734282, compound

HRID 1973710Notes

Reaction equation

HRID 1973710 reaction equation
[C:1]([C:5]1[CH:12]=[C:11]([CH3:13])[C:8]([CH2:9]Cl)=[C:7]([CH3:14])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[C:16]([OH:27])(=[O:26])[C:17]1[CH:25]=[CH:24][CH:23]=[C:19]([C:20]([OH:22])=[O:21])[CH:18]=1.C(N([CH2:33][CH3:34])CC)C.CN(C)[CH:37]=[O:38]>O.C(O)(=O)C.C(O)C>[C:1]([C:5]1[CH:12]=[C:11]([CH3:13])[C:8]([CH2:9][O:21][C:20](=[O:22])[C:19]2[CH:23]=[CH:24][CH:25]=[C:17]([C:16]([O:27][CH2:9][C:8]3[C:7]([CH3:14])=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[C:37]([OH:38])[C:33]=3[CH3:34])=[O:26])[CH:18]=2)=[C:7]([CH3:14])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8496Isophthalic AcidHCID 901316-tert-Butyl-3-(chloromethyl)-2,4-dimethylphenol

Product 1

HCID 86734282HCID 86734282, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 34 g. (0.15 mole) of 4-tert.-butyl-3-hydroxy-2,6-dimethylbenzyl chloride, 12.5 g. (0.075 mole) of isophthalic acid, and 18.25 g. (0.18 mole) of triethylamine in 35 ml. of dimethylformamide was heated at a temperature of 97°-100° C. for a period of 162/3 hours. The hot melt was added to 300 g. of ice slurry to form 43 g. of a semisolid. This was extracted with 300 ml. of benzene and the benzene solution decolorized with charcoal. The filtrate was concentrated in vacuo to give 36 g. of a light amber colored oil. This was dissolved in 40 ml. of ethanol and diluted with 150 ml. of acetic acid. The mixture was added to 250 ml. of water to give 30 g. of a tan amorphous powder. Further purification was carried out by chromatography on aluminum oxide using chloroform to obtain 26 g. of an amber oil. On standing, the oil gave 14 g. of cream colored crystals, m.p. 155°-156° C. Anal. calc'd.: C=74.73, H=7.69; Found: C=75.15, H=7.62.

Workup

  1. additionA mixture of 34 g
  2. additionThe hot melt was added to 300 g
  3. customof ice slurry to form 43 g
  4. extractionThis was extracted with 300 ml
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give 36 g
  7. dissolutionThis was dissolved in 40 ml
  8. additionThe mixture was added to 250 ml
  9. customFurther purification
  10. customto obtain 26 g
  11. customthe oil gave 14 g

Sources & evidence

ORD record
ord-8305ff8abdc64701bf55da4876082c79
Source dataset
uspto-grants-1976_12
Patent number
US03998863

Reaction notes

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