4-Methylmorpholine → Methyl 4-hydroxymethyl-2-phenylbenzoate

HRID 325214Notes

Reaction equation

HRID 325214 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN1CCOCC1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:12]=[CH:11][C:7]([CH2:8][OH:9])=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 857324742-Phenylterephthalic acid mono methyl ester

Product 1

HCID 10824066Methyl 4-hydroxymethyl-2-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The resultant acid from Example 16A (1.0 equivalent) is treated with a slight excess of N-methylmorpholine (1.1 equivalent) and isobutylchworoformate (1.0 equivalent) in THF at 0° C. The mixture is then treated with NaBH4 (1.0 equivalent) and aqueous NaHCO3 and stirred at 0° C. until the reaction is judged complete by TLC analysis. The mixture is poured into dilute aqueous acid and extracted into ethyl acetate which is dried and evaporated. The product is purified by chromatography on silica gel.

Workup

  1. additionThe mixture is poured into dilute aqueous acid
  2. extractionextracted into ethyl acetate which
  3. customis dried
  4. customevaporated
  5. customThe product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a3f88e225bb745acb9b20d631915180d
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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