Methanol → Methyl 4'-(hydroxymethyl)[1,1'-biphenyl]-3-carboxylate

HRID 967116Notes

Reaction equation

HRID 967116 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:9][C:10]=1C=O)=[O:4].[BH4-].[Na+].[CH3:21][OH:22]>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:14]=[CH:15][C:16]([CH2:21][OH:22])=[CH:17][CH:18]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86586632Methyl 4-formyl[1,1′-biphenyl]-3-carboxylate

Product 1

HCID 20100116Methyl 4'-(hydroxymethyl)[1,1'-biphenyl]-3-carboxylate

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 1.56 g (6.5 mmol.) 4-formyl-biphenyl-3-carboxylic acid methyl ester in 30 mL methanol at 0° C. was added 307 mg (8.1 mmol.) sodium borohydride. The mixture was stirred at 0° C. for 1 hour, then quenched with saturated ammonium chloride solution. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extracts were combined, washed successively with water, brine then dried (MgSO4) and concentrated in vacuo to yield an oil. Chromatography on Silica Gel eluting with ethyl acetate/hexanes (1:5) afforded 1.5 g 4′-hydroxymethyl-biphenyl-3-carboxylic acid methyl ester as an oil.

Workup

  1. customquenched with saturated ammonium chloride solution
  2. additionThe mixture was poured into water
  3. extractionextracted with ethyl acetate
  4. washwashed successively with water, brine
  5. dry with materialthen dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto yield an oil

Sources & evidence

ORD record
ord-414b236a171d4888b7bc744ffcf33463
Source dataset
uspto-grants-2005_10
Patent number
US06953810B2

Reaction notes

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