Ethyl Acetate → HCID 131732068, compound

HRID 339852Notes

Reaction equation

HRID 339852 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=1)[CH2:12]OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:21]([O-:24])([O-:23])=[O:22].[Na+:25].[Na+].C(OCC)(=O)C>O>[Na+:25].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][S:21]([O-:24])(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 22086784HCID 22086784, compound

Product 1

HCID 131732068HCID 131732068, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

5.80 g of methanesulfonic acid 3-benzyloxybenzyl ester and 5.21 g of sodium sulfite were dissolved in 50 ml of water and stirred at 90° C. for 5 hours. The mixture was allowed to cool to room temperature overnight, then 30 ml of ethyl acetate were added and the mixture was stirred in an ice bath for 1 hour. The precipitate was filtered off with suction, washed twice with 10 ml of ice-water and twice with 10 ml of ice-cold ethyl acetate, and dried in a vacuum drying cabinet at 40° C. overnight. This gave the product (2.37 g) with a molecular weight of 300.3 g/mol (C14H13O4S.Na); MS (ESI): m/e=296 (M−Na++H2O+H+).

Workup

  1. temperatureto cool to room temperature overnight
  2. stirringthe mixture was stirred in an ice bath for 1 hour
  3. filtrationThe precipitate was filtered off with suction
  4. washwashed twice with 10 ml of ice-water and twice with 10 ml of ice-cold ethyl acetate
  5. customdried in a vacuum
  6. customdrying cabinet at 40° C. overnight

Sources & evidence

ORD record
ord-58c450d10bcf43c3892244625855f4c7
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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