2,4-Dimethylphenol → HCID 18961265, compound

HRID 1708259Notes

Reaction equation

HRID 1708259 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[C:10]([CH2:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19](O)[C:20]([OH:22])=O)=[CH:17][CH:16]=1)([OH:12])=[O:11].[CH2:26](O)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]2[O:9][C:20](=[O:22])[CH:19]([C:18]3[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:10]([O:12][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH3:26])=[O:11])=[CH:25][CH:24]=3)[C:4]=2[CH:5]=1

Participants

6

Reactant 3

HCID 77712,4-DimethylphenolHCID 8221Stearyl AlcoholHCID 10998701100304-15-2

Product 1

HCID 18961265HCID 18961265, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of 18.3 g (0.15 mol) of 2,4-dimethylphenol and 11.3 g (0.05 mol) of 4-carboxymethoxymandelic acid is stirred at about 185° C. for 3.5 hours. Excess 2,4-dimethylphenol is then distilled off in a high vacuum. 12.5 g (0.046 mol) of 1-octadecanol and 0.3 g (1.58 mmol) of p-toluenesulfonic acid are added to the residue, and the mixture is maintained at about 185° C. under a slight vacuum (50 mbar) for 1.5 hours. The reaction mixture is diluted with 50 ml of toluene and washed with water. The organic phases are combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. Crystallisation of the residue from acetonitrile gives 9.9 g (38%) of 5,7-dimethyl-3-(4-n-octadecyloxycarbonylmethoxyphenyl)benzofuran-2-one, melting point 57°-59° C. (Compound (109), Table 1).

Workup

  1. distillationExcess 2,4-dimethylphenol is then distilled off in a high vacuum
  2. temperaturethe mixture is maintained at about 185° C. under a slight vacuum (50 mbar) for 1.5 hours
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated on a vacuum rotary evaporator
  6. customCrystallisation of the residue from acetonitrile

Sources & evidence

ORD record
ord-0510824d6b8c440a891d4b16a861d195
Source dataset
uspto-grants-1994_10
Patent number
US05356966

Reaction notes

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