3-Hydroxybenzyl alcohol → (3-Isopropoxyphenyl)methanol

HRID 2242357Notes

Reaction equation

HRID 2242357 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].I[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH:11]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 6362Isopropyl iodideHCID 10796Cesium carbonate

Product 1

HCID 2759474(3-Isopropoxyphenyl)methanolYield 123.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-hydroxybenzyl alcohol (2.00 g, 0.014 mol), 2-iodopropane (2.4 ml, 8.29 mmol), cesium carbonate (8.00 g, 0.0246 mol) in DMF (10 ml) was heated at 85° C. for 8 h. The reaction was diluted with water (100 ml) and extracted with DCM (30 ml) and this was washed with water (2×30 ml). The product was chromatographed on silica using DCM:methanol (19:1) to afford 3-isopropoxybenzyl alcohol (1.70 g, 73%) as an orange liquid.

Workup

  1. extractionextracted with DCM (30 ml)
  2. washthis was washed with water (2×30 ml)
  3. customThe product was chromatographed on silica

Sources & evidence

ORD record
ord-9af2100cf6854f00890c31880a928670
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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