3-Methyl-2-butenoic acid → HCID 9834436, compound

HRID 2120331Notes

Reaction equation

HRID 2120331 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][C:15]([CH3:20])=[CH:16][C:17]([OH:19])=[O:18]>Cl>[CH3:9][C:4]1[CH:5]=[C:6]([C:15]([CH3:20])([CH3:14])[CH2:16][C:17]([OH:19])=[O:18])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 109313-Methyl-2-butenoic acidHCID 336372-MethylanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 9834436HCID 9834436, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 2-methoxytoluene (146.7 g, 1.2 mol), aluminum chloride (44 g, 0.33 mol) and 3-methylcrotonic acid (30 g, 0.3 mol) were added, and the mixture was stirred at room temperature for 24 hours, and thereafter the reaction was stopped by the addition of six normal (6-N) hydrochloric acid aqueous solution (300 ml) thereto. Subsequently, from the thus-obtained mixture, the organic material was extracted with diethyl ether (150 ml). After that, one normal (1-N) caustic soda aqueous solution (100 ml) was added to the organic layer for extraction of the carboxylic acid(s). The thus-obtained alkaline mixture was acidified by the addition of hydrochloric acid (HCl) aqueous solution, and the mixture was extracted with diethyl ether and the solvent therein was removed by distillation. The thus-obtained residue was re-crystallized with hexane to obtain 3-(3-methyl-4-methoxyphenyl)-3-methylbutyric acid (39.6 g, yield: 59%).

Workup

  1. extractionSubsequently, from the thus-obtained mixture, the organic material was extracted with diethyl ether (150 ml)
  2. additionAfter that, one normal (1-N) caustic soda aqueous solution (100 ml) was added to the organic layer for extraction of the carboxylic acid(s)
  3. additionThe thus-obtained alkaline mixture was acidified by the addition of hydrochloric acid (HCl) aqueous solution
  4. extractionthe mixture was extracted with diethyl ether
  5. customthe solvent therein was removed by distillation
  6. customThe thus-obtained residue was re-crystallized with hexane

Sources & evidence

ORD record
ord-0450d9f6f7ca49eaa6d0f58f01c19af7
Source dataset
uspto-grants-2004_02
Patent number
US06689902B2

Reaction notes

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