Methanol → 3-Phenoxybenzaldehyde

HRID 1395123Notes

Reaction equation

HRID 1395123 reaction equation
[S:1](S([O-])=O)([O-:4])(=[O:3])=[O:2].[Na+].[Na+].[O:10]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO>O.C(OC(C)C)(C)C>[S:1](=[O:2])([OH:4])[O-:3].[O:10]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 382843-PhenoxybenzaldehydeHCID 656671Sodium Pyrosulfite

Product 2

HCID 382843-PhenoxybenzaldehydeYield 95.5%HCID 104748Bisulfite

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A solution of 200 g of sodium metabisulfite in 800 ml of water was added to a solution of 200 g of m-phenoxy-benzaldehyde in 800 ml of isopropyl ether and after the addition of 250 ml of methanol, the mixture was stirred for 3 hours and was vacuum filtered. The recovered precipitate was washed with 1--1 water-methanol mixture and then with isopropyl ether and was dried to obtain 295 g of the combination bisulfite of m-phenoxy-benzaldehyde (titer of 95.5% mobile hydrogen). The product was crystallized from 4 volumes of ethyl acetate to obtain a 97.6% yield of the product with a titer of mobile hydrogen of 98%.

Workup

  1. filtrationfiltered
  2. washThe recovered precipitate was washed with 1--1 water-methanol mixture
  3. dry with materialwith isopropyl ether and was dried

Sources & evidence

ORD record
ord-141b17c4d9984fa78d56506b6063d7ed
Source dataset
uspto-grants-1980_05
Patent number
US04202835

Reaction notes

Loading…