p-Toluenesulfonic acid → HCID 53734620, compound

HRID 1979509Notes

Reaction equation

HRID 1979509 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]([OH:14])=[O:13])[CH2:4][CH2:3]1.[C:16]1(C)C=CC(S(O)(=O)=O)=C[CH:17]=1>>[CH2:16]([O:13][C:12]([CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH3:15])([CH3:1])[CH2:3][CH2:4]1)=[O:14])[CH3:17]

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 204393164,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

Product 1

HCID 53734620HCID 53734620, compoundYield 63%

Procedure

248 g of 1,1-dimethyl-tetralin-4-carboxylic acid in 1.740 liters of absolute alcohol are held at reflux temperature for 6 hours with 24.8 g of paratoluenesulphonic acid in a 3-liter flask provided with a thermometer, stirrer and reflux condenser. The excess alcohol is then distilled off under a slight vacuum and the residue is poured into ice/water. The mixture is extracted with ether, washed neutral, dried, filtered, evaporated and distilled, there being thus obtained 177 g of 1,1-dimethyl-tetralin-4-carboxylic acid ethyl ester of boiling point 74° C./0.03 mmHg; nD20 =1.5153; yield 63%. Odour: faint, jasmone-like.

Workup

  1. customprovided with a thermometer, stirrer
  2. temperaturereflux condenser
  3. distillationThe excess alcohol is then distilled off under a slight vacuum
  4. additionthe residue is poured into ice/water
  5. extractionThe mixture is extracted with ether
  6. washwashed neutral
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. distillationdistilled

Sources & evidence

ORD record
ord-7af3d0a61d454ad380f15e9c93d28dd3
Source dataset
uspto-grants-1984_11
Patent number
US04481133

Reaction notes

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