Hydrochloric Acid → (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluenesulphonyloxy-2-butanol

HRID 653202Notes

Reaction equation

HRID 653202 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7](C)=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:12][O:13][C:14]1[C:19]([CH3:20])=[C:18]([CH3:21])[C:17]([O:22][CH3:23])=[C:16]([CH3:24])[C:15]=1[CH2:25][CH2:26][C@:27]([CH3:31])([OH:30])[CH2:28][OH:29].N1C=CC=C[CH:33]=1.Cl>C(Cl)Cl>[CH3:12][O:13][C:14]1[C:19]([CH3:20])=[C:18]([CH3:21])[C:17]([O:22][CH3:23])=[C:16]([CH3:24])[C:15]=1[CH2:25][CH2:26][C@:27]([CH3:31])([OH:30])[CH2:28][O:29][S:1]([C:4]1[C:5]([CH3:33])=[CH:6][CH:7]=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 11129761(S)-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1,2-butanediol

Product 1

HCID 86740735(S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluenesulphonyloxy-2-butanolYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

237 mg of tosyl chloride and 350 mg of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-butanediol are dissolved in 1 ml of methylene chloride. 0.180 ml of pyridine are then added dropwise at 0° C. and the mixture is left to stand at 0° C. for 1 hour and then at room temperature for 16 hours. Thereupon, 1 g of ice and 0.3 ml of concentrated hydrochloric acid are added. The mixture is then extracted with methylene chloride, and the extract is dried and concentrated. There are obtained 511 mg (95%) of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluenesulphonyloxy-2-butanol.

Workup

  1. waitthe mixture is left
  2. waitat room temperature for 16 hours
  3. extractionThe mixture is then extracted with methylene chloride
  4. customthe extract is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-29444116a8c64bac8b05b7b4a6f94bb5
Source dataset
uspto-grants-1987_06
Patent number
US04675421

Reaction notes

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