Hydrochloric Acid → 4-(1-Hydroxy-2,2-dimethoxyethyl)-2,5-dimethylphenol

HRID 747583Notes

Reaction equation

HRID 747583 reaction equation
[OH-].[Na+].[C:3]1([OH:11])[C:4]([CH3:10])=[CH:5][CH:6]=[C:7]([CH3:9])[CH:8]=1.[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH:15]=[O:16].Cl>C(#N)C.O>[OH:16][CH:15]([C:6]1[C:7]([CH3:9])=[CH:8][C:3]([OH:11])=[C:4]([CH3:10])[CH:5]=1)[CH:14]([O:17][CH3:18])[O:13][CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72672,5-DimethylphenolHCID 14798Sodium HydroxideHCID 162650Acetaldehyde, 2,2-dimethoxy-

Product 1

HCID 117758724-(1-Hydroxy-2,2-dimethoxyethyl)-2,5-dimethylphenolYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of an aqueous solution of 5.2% sodium hydroxide (630 g), 2,5-xylenol (100 g), an aqueous solution of 60% glyoxal dimethyacetal (213 g) and water (200 g) was heated at 55° C. for 5 hours with stirring. The reaction mixture was cooled in an ice bath, and to the mixture were added acetonitrile (90 g) and 7.4% hydrochloric acid (380 g) successively. The precipitating crystals were filtered to give 4-(1-hydroxy-2,2-dimethoxyethyl)-2,5-dimethylphenol (150 g).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationThe precipitating crystals were filtered

Sources & evidence

ORD record
ord-3155425f35374c409c8b979cdd160d5f
Source dataset
uspto-grants-2008_07
Patent number
US07396954B2

Reaction notes

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