3-Isopropoxybenzaldehyde → (3-Isopropoxyphenyl)methanol

HRID 1641321Notes

Reaction equation

HRID 1641321 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:8][OH:9])[CH:10]=[CH:11][CH:12]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7129143-IsopropoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2759474(3-Isopropoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-Isopropoxy-benzaldehyde 14-1 (20 g, 122 mmol) in methanol (400 mL), sodium borohydride (5 g) is added in several portions at 0° C. The resulting mixture is then stirred at rt for 3 h. The reaction is quenched by addition of saturated NH4OH. Extracted (EtOAc), concentrated, a colorless oil 14-2 (MH+, 166) is obtained and use without purification. Re-dissolve (3-Isopropoxy-phenyl)-methanol 14-2 in ether (244 mL) PBr3 (11.5 mL, 122 mmol) is added dropwise at 0° C. The reaction mixture is stirred at 0° C. then rt for 3 h, quenched (MeOH), extracted (EtOAc), concentrated, a colorless oil 14-3 is obtained. (MH+, 288)

Workup

  1. customThe reaction is quenched by addition of saturated NH4OH
  2. extractionExtracted (EtOAc)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9b2c13d0c66343cfb3624aefac3452ac
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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