p-Toluenesulfonic acid → HCID 21491871, compound

HRID 1973501Notes

Reaction equation

HRID 1973501 reaction equation
[O:1]=[C:2]1[CH2:7][C:6](=[O:8])[CH2:5][CH:4]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:3]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+].[CH2:38]([O:40][CH2:41][CH2:42]O)[CH3:39]>>[CH2:38]([O:40][CH2:41][CH2:42][O:8][C:6]1[CH2:5][CH:4]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:2](=[O:1])[CH:7]=1)[CH3:39]

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8076Glycol monoethyl etherHCID 10340Sodium CarbonateHCID 20239929HCID 20239929, compound

Product 1

HCID 21491871HCID 21491871, compound

Procedure

A mixture of ethyl 2,4-dioxo-6-p-tolylcyclohexanecarboxylate (5 g.) prepared as in Example 1, and p-toluenesulphonic acid (0.5 g.) dissolved in 2-ethoxyethanol (50 ml.) was allowed to stand at 25° C for 16 hrs. Pouring the mixture into excess aqueous Na2CO3 solution followed by ether extraction afforded a mauve coloured solution containing the product. After decolourisation of the solution with activated charcoal, evaporation of solvents and crystallisation of the residue from ether/cyclohexane afforded ethyl 4-ethoxyethoxy-2-oxo-6-p-tolyl-3cyclohexenecarboxylate m.p. 59°-60° C.

Workup

  1. extractionfollowed by ether extraction
  2. customafforded a mauve coloured solution
  3. additioncontaining the product
  4. customAfter decolourisation of the solution with activated charcoal, evaporation of solvents and crystallisation of the residue from ether/cyclohexane

Sources & evidence

ORD record
ord-3a2892981c214ba7b4748adadcc903af
Source dataset
uspto-grants-1976_12
Patent number
US03997590

Reaction notes

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