Chloromethyl Methyl Ether → 3-Benzyloxy-4-methoxybenzaldehyde

HRID 652800Notes

Reaction equation

HRID 652800 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[OH:17])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20]OCCl>CN(C)C=O.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:20])[CH:12]=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride2×HCID 110206353-Benzyloxy-4-hydroxybenzaldehyde

Product 1

HCID 806713-Benzyloxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 300 g of 3-benzyloxy-4-hydroxybenzaldeyde (obtained as described in example 62) in 600 ml of dimethylformamide was added to a suspension of 34.6 g of sodium hydride in 346 ml of dimethylformamide under stirring in nitrogen atmosphere. After complete dissolution of sodium hydride 116 g of chloromethyl methyl ether were added; stirring was continued for 30 minutes. The mixture was then diluted with water and extracted with ethyl ether. The combined organic phase was dried over sodium sulfate, filtered and evaporated. The residue was distilled (b.p. 178°-183° C./0.1 mm Hg) to give 3-benzyloxy-4-methoxybenzaldehyde, m.p. 30° C. (from petroleum ether, b.p. 30°-70° C.).

Workup

  1. additionwere added
  2. stirringstirring
  3. extractionextracted with ethyl ether
  4. dry with materialThe combined organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. distillationThe residue was distilled (b.p. 178°-183° C./0.1 mm Hg)

Sources & evidence

ORD record
ord-95efb3875a0543a7a9361ee7cf4d6162
Source dataset
uspto-grants-1987_06
Patent number
US04673671

Reaction notes

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