p-Toluenesulfonic acid → HCID 23466449, compound

HRID 1439456Notes

Reaction equation

HRID 1439456 reaction equation
C1C[O:17][C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:15][OH:16])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])([CH3:4])O1.N1C=CC=CC=1[CH2:25][C:26](OC(=O)CC1C=CC=CN=1)=[O:27].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[C:26]([O:16][CH2:15]/[C:8](/[CH2:9][CH2:10][CH:11]=[C:12]([CH3:13])[CH3:14])=[CH:7]\[CH2:6][CH2:5][C:3](=[O:17])[CH3:4])(=[O:27])[CH3:25]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 54303403HCID 54303403, compoundHCID 74054346HCID 74054346, compound

Product 1

HCID 23466449HCID 23466449, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.2 g of the alcohol thus obtained was acetylated with anhydrous pyridine-acetic anhydride in the usual way and dissolved in 70 ml of methanol. To this solution was added 70 mg of p-toluenesulfonic acid, and the mixture was allowed to stand overnight at room temperature. The resultant was neutralized with an aqueous sodium hydrogencarbonate solution and extracted with n-hexane. There was obtained 7.2 g of the desired product.

Workup

  1. extractionextracted with n-hexane

Sources & evidence

ORD record
ord-277b3ebb7e3b4ac592be2284e0703926
Source dataset
uspto-grants-1977_11
Patent number
US04059641

Reaction notes

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