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

HRID 480083Notes

Reaction equation

HRID 480083 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-ea64aba55ce14c4696dff9860263f1a5
Source dataset
uspto-grants-2003_11
Patent number
US06649633B2

Reaction notes

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