Acetate → 4397-13-1

HRID 1721412Notes

Reaction equation

HRID 1721412 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[OH:11].C=O.[C:14]([O-])(=[O:16])C>O.C(O)(=O)C>[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:14][OH:16])[C:5]=1[OH:11]

Participants

7

Reactant 4

HCID 175AcetateHCID 712FormaldehydeHCID 77712,4-Dimethylphenol2×HCID 14798Sodium Hydroxide

Product 1

HCID 114805504397-13-1Yield 97.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

75 g of NaOH were dissolved in 300 ml of deionized (DI) water. 183.3 g 2,4-dimethylphenol were added, and the mixture was cooled to 15°-20° C. 188 g of aqueous formaldehyde (made from 152g 37% formalin diluted with 36 g water) were added over half an hour, while the temperature was maintained below 20° C. After stirring overnight, Thin Layer Chromotography (TLC) in 2:1 hexane/ethyl. acetate showed a single spot, and no remaining 2,4-dimethylphenol. The pH was then adjusted to 6-7 with about 200 ml of 50% aqueous acetic acid. The mixture was transferred to a 2 liter beaker, and extracted with ethyl acetate (400 ml). Removal of the ethyl acetate in a vacuum gave 221.0 g (97.4%) of the desired product as a clear oil or a low-melting solid.

Workup

  1. temperaturethe mixture was cooled to 15°-20° C
  2. temperaturewas maintained below 20° C
  3. extractionextracted with ethyl acetate (400 ml)
  4. customRemoval of the ethyl acetate in a vacuum

Sources & evidence

ORD record
ord-93fc56c0630f40029b32ba4b3f30e030
Source dataset
uspto-grants-1996_04
Patent number
US05510420

Reaction notes

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