tert-Butyl methyl ether → HCID 131732067, compound

HRID 339824Notes

Reaction equation

HRID 339824 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:17]([O-:20])([O-:19])=[O:18].[Na+:21].[Na+].COC(C)(C)C>O>[Na+:21].[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][S:17]([O-:20])(=[O:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 24437Sodium SulfiteHCID 700424-Benzyloxybenzyl chloride

Product 1

HCID 131732067HCID 131732067, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 25.51 g of 4-benzyloxybenzyl chloride and 28.78 g of sodium sulfite in 96 ml of water was stirred at 75° C. for 21 hours. After cooling to room temperature, the reaction solution was stirred with 100 ml of tert-butyl methyl ether, and the solids were filtered off with suction, washed twice with 20 ml of tert-butyl methyl ether, once with 20 ml of ice-water, twice with 20 ml of acetone and twice with 20 ml of dichloromethane. The precipitate was dried in a vacuum drying cabinet at 40° C. overnight. This gave the product (6.20 g) with a molecular weight of 300.3 g/mol (C14H13O4S.Na); MS (ESI): m/e=301 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solids were filtered off with suction
  3. washwashed twice with 20 ml of tert-butyl methyl ether, once with 20 ml of ice-water, twice with 20 ml of acetone and twice with 20 ml of dichloromethane
  4. customThe precipitate was dried in a vacuum
  5. customdrying cabinet at 40° C. overnight

Sources & evidence

ORD record
ord-0a09557ce558438d85acafe4aee061c7
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

Loading…