Hydrochloric Acid → Methyl 2-methyl-2-hydroxymethyl-3-(4-chlorophenyl)-3-keto-propanoate

HRID 1607213Notes

Reaction equation

HRID 1607213 reaction equation
[CH3:1][CH:2]([C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8])[C:3]([O:5][CH3:6])=[O:4].[CH2:16]=[O:17].N1C=CC=CC=1.Cl>CO.CCOCC>[CH3:1][C:2]([CH2:16][OH:17])([C:7]([C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:8])[C:3]([O:5][CH3:6])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1049PyridineHCID 19852612Methyl 3-(4-chlorophenyl)-2-methyl-3-oxopropanoate

Product 1

HCID 19852106Methyl 2-methyl-2-hydroxymethyl-3-(4-chlorophenyl)-3-keto-propanoateYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

Into a 5 liter RBF is placed 1000 g (4.37 mole) of methyl 2-methyl-3-(4-chlorophenyl)-3-keto-propanoate, 157 g (5.25 mole) of paraformaldehyde, 1000 ml of pyridine, and 50 g of Triton B (40% in MeOH). The resulting mixture was heated 50° C. for 2 hours. After cooling to room temperature, the reaction mixture was transferred to a 12 liter separatory funnel and 1.5 liters of ether and 2 kgs of ice are added. The mixture is slowly acidified by 1.0 liters of conc HCl and the organic phase is separated, washed with 2 liters of brine and dried over MgSO4. On concentration, it affords 1100 g (100%) of a red oil, methyl 2-methyl-2-hydroxymethyl-3-(4-chlorophenyl)-3-keto-propanoate. NMR data was consistent with the structure.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was transferred to a 12 liter separatory funnel
  3. customthe organic phase is separated
  4. washwashed with 2 liters of brine
  5. dry with materialdried over MgSO4
  6. concentrationOn concentration, it

Sources & evidence

ORD record
ord-6c3cef5e0e764428a9a513db29e28e44
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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