p-Toluenesulfonic acid → HCID 70431262, compound

HRID 2107838Notes

Reaction equation

HRID 2107838 reaction equation
[CH3:1][C:2]1([CH3:14])[C@@H:4]([CH:5](O)[C:6]([CH3:9])([CH3:8])[CH3:7])[C@H:3]1[C:11]([OH:13])=[O:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:14])[C@H:3]2[C@@H:4]1[C@H:5]([C:6]([CH3:9])([CH3:8])[CH3:7])[O:12][C:11]2=[O:13]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 53701436HCID 53701436, compound

Product 1

HCID 70431262HCID 70431262, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5 g of the product of Step A in 50 ml of benzene was heated to reflux and 20 mg of p-toluene sulfonic acid were added thereto and reflux was continued for 15 minutes. The mixture was cooled and was washed with aqueous sodium hydroxide and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 9-1 benzene-ethyl acetate mixture to obtain (1R,4R,5S) 6,6-dimethyl-4-(2-methyl-prop-2-yl)-3-oxa-bicyclo (3,1,0) hexan-2-one melting at 113° C.

Workup

  1. temperatureto reflux
  2. temperaturereflux
  3. temperatureThe mixture was cooled
  4. washwas washed with aqueous sodium hydroxide
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with a 9-1 benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-a497087a8ae74a34a65684b1eba1a6e6
Source dataset
uspto-grants-1990_06
Patent number
US04935532

Reaction notes

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