Methanol → BENZYL 2-HYDROXYMETHYLBENZOATE

HRID 1756423Notes

Reaction equation

HRID 1756423 reaction equation
C([C:3]1[CH:18]=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:5][CH:4]=1)=O.C1C[O:22][CH2:21]C1.CO.[BH4-].[Na+]>O>[OH:22][CH2:21][C:5]1[CH:4]=[CH:3][CH:18]=[CH:17][C:6]=1[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 11528845Benzyl 4-formylbenzoate

Product 1

HCID 11356918BENZYL 2-HYDROXYMETHYLBENZOATE

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.3 g (43 mmol) of benzyl 4-formylbenzoate, 50 ml of THF and 50 ml of methyl alcohol are introduced into a round-bottomed flask. While cooling in an icebath, 820 mg (21.5 mmol) of sodium borohydride are added in small portions and the mixture is stirred at room temperature for two hours. The reaction medium is poured into water, the mixture is extracted with ethyl ether and the organic phase is separated after settling has taken place, dried over magnesium sulphate and evaporated. 10.4 g (100%) of the expected product, melting point 55°-56° C., are collected.

Workup

  1. additionare added in small portions
  2. extractionthe mixture is extracted with ethyl ether
  3. customthe organic phase is separated after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom10.4 g (100%) of the expected product, melting point 55°-56° C., are collected

Sources & evidence

ORD record
ord-d56683a6fac74f23abc6f32b1e6fcff9
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

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