4-Toluenesulfonyl chloride → p-Toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester

HRID 1762580Notes

Reaction equation

HRID 1762580 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][CH:20]([CH2:24][OH:25])[CH2:21]2)=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][CH:20]([CH2:24][O:25][S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[CH2:21]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10797825(7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

Product 1

HCID 11210176p-Toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20.96 g (110 mmol) of p-toluenesulphonic acid chloride are added at room temperature, while stirring, to a solution of 19.2 g (100 mmol) of 7-methoxy-1,2,3,4-tetrahydro-naphthalene-2-methanol in 80 ml of absolute pyridine, the slightly exothermic reaction being maintained at room temperature with an ice bath. The reaction mixture is stirred at room temperature for 1 hour to complete the reaction and is then diluted with ice-water and extracted with diethyl ether. The organic phase is washed while ice-cold with 2N hydrochloric acid and water, is dried over sodium sulphate, filtered and concentrated by evaporation under reduced pressure. The resulting oil is crystallised from diethyl ether/pentane to yield p-toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester of m.p. 64°-66 °.

Workup

  1. customthe slightly exothermic reaction
  2. customthe reaction
  3. extractionextracted with diethyl ether
  4. washThe organic phase is washed while ice-cold with 2N hydrochloric acid and water
  5. dry with materialis dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe resulting oil is crystallised from diethyl ether/pentane

Sources & evidence

ORD record
ord-be662b22142e48788f1767714c267279
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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