p-Toluenesulfonic acid → HCID 70431262, compound

HRID 256226Notes

Reaction equation

HRID 256226 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-dac15778436f44c2aa0b418013394f03
Source dataset
uspto-grants-1987_10
Patent number
US04701542

Reaction notes

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