p-Toluenesulfonic acid → HCID 18961269, compound

HRID 1708258Notes

Reaction equation

HRID 1708258 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]([CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[C:35]3[CH:36]=[C:37]([CH3:40])[CH:38]=[CH:39][C:34]=3[O:33][C:32]2=[O:41])=[CH:27][CH:26]=1)(O)=[O:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:40][C:37]1[CH:38]=[CH:39][C:34]2[O:33][C:32](=[O:41])[CH:31]([C:28]3[CH:27]=[CH:26][C:25]([O:24][CH2:23][C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:21])=[CH:30][CH:29]=3)[C:35]=2[CH:36]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8221Stearyl AlcoholHCID 18961263HCID 18961263, compound2×

Product 1

HCID 18961269HCID 18961269, compound

Conditions

Temperature
200 °C

Procedure

A mixture of 5.0 g (18.5 mmol) of 1-octadecanol, 5.0 g (16.8 mmol) of 3-(4-carboxymethoxyphenyl)-5-methylbenzofuran-2-one (Compound (101), Example 1) and 1.0 g (5.3 mmol) of p-toluenesulfonic acid is stirred at 200° C. under a slight vacuum (150 mmHg) for about 1 hour. The reaction mixture is then diluted with 60 ml of ligroin and cooled with ice/water. The precipitated product is filtered. Crystallisation of the residue due from ligroin given 7.5 g (81%) of 5-methyl-3-(4-n-octadecyloxycarbonylmethoxyphenyl)benzofuran-2-one, melting pint 85°-87° C. (Compound (105), Table 1).

Workup

  1. filtrationThe precipitated product is filtered
  2. customCrystallisation of the residue due from ligroin
  3. custompint 85°-87° C. (Compound (105), Table 1)

Sources & evidence

ORD record
ord-76ffaab2129e4731964128aaf5788205
Source dataset
uspto-grants-1994_10
Patent number
US05356966

Reaction notes

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