Toluene → HCID 59439477, compound

HRID 1640060Notes

Reaction equation

HRID 1640060 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([OH:6])=O.CS(O)(=O)=[O:10].C([O:21][CH2:22][CH2:23][C:24]1[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[CH:26][C:25]=1[OH:32])(=O)C1C=CC=CC=1.[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O>[C:39]([O:21][CH2:22][CH2:23][C:24]1[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[C:26]2[C:25]=1[O:32][C:2]([CH3:7])([CH3:1])[CH2:3][C:4]2=[O:6])(=[O:10])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6395Methanesulfonic AcidHCID 109313-Methyl-2-butenoic acidHCID 59439463HCID 59439463, compound

Product 1

HCID 59439477HCID 59439477, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

202.2 g (2.020 mol) of 3-methylcrotonic acid and 2 L of methanesulfonic acid were put into a 10 L four-necked round bottom flask and stirred on a 50° C. water bath in stream of nitrogen. 500.0 g (1.836 mol) of 2-(2-hydroxy-6-methoxyphenyl)ethyl benzoate obtained in Example 4 was added to this solution. The reaction mixture was stirred at the same temperature for 1.8 hours and ice cooled. 2.5 L of toluene was added to the reaction mixture and subsequently 5 L of water was added dropwise for about 1 hour. The contents were transferred to a 20 L separatory funnel and allowed to be separated and the aqueous layer was discarded. The organic layer was washed three times with water (5 L×3) and concentrated in vacuo on a 40° C. bath and 846.1 g of the title compound was obtained.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 1.8 hours
  2. temperatureice cooled
  3. additionwas added dropwise for about 1 hour
  4. customThe contents were transferred to a 20 L separatory funnel
  5. customto be separated
  6. washThe organic layer was washed three times with water (5 L×3)
  7. concentrationconcentrated in vacuo on a 40° C. bath

Sources & evidence

ORD record
ord-805233ddafd0490d971cd17fc01b4f59
Source dataset
uspto-grants-2012_02
Patent number
US08110688B2

Reaction notes

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