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

HRID 383085Notes

Reaction equation

HRID 383085 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.C(OC(Cl)=O)C(C)C.[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

7

Reactant 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 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 isobutylchloroformate (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-9fc20771f00a461ba7a0afd8ae1c5ffe
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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