4-Hydroxybenzaldehyde → Phenol, 4-(dimethoxymethyl)-

HRID 654217Notes

Reaction equation

HRID 654217 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][CH:3]=1.CO.CO[CH:14]([O:17][CH3:18])[O:15][CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>>[CH3:18][O:17][CH:14]([O:15][CH3:16])[C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

6

Reactant 5

HCID 1264-HydroxybenzaldehydeHCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 516892Sodium Bicarbonate

Product 1

HCID 11052043Phenol, 4-(dimethoxymethyl)-

Procedure

A mixture of 4.88 g (40 mmol) of 4-hydroxybenzaldehyde, 6.6 g (206 mmol) of methanol and 5.1 g (48 mmol) of trimethylorthoformate and 28 mg of p-toluene sulfonic acid was stirred at room temperature for 12 h. An excess of NaHCO3 was then added and the mixture stirred for a further 60 h. The mixture was then filtered, the solvent removed in-vacuo and the residue purified by flash chromatography (silica; 20% ethyl acetate in hexanes) to give the title compound as a viscous oil.

Workup

  1. stirringthe mixture stirred for a further 60 h
  2. filtrationThe mixture was then filtered
  3. customthe solvent removed in-vacuo
  4. customthe residue purified by flash chromatography (silica; 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0ee1d816a9d74d479dd345a4b7f24d3f
Source dataset
uspto-grants-1992_07
Patent number
US05130335

Reaction notes

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