Hydrochloric Acid → [4-Methoxy-3-(propan-2-yl)phenyl]methanol

HRID 352557Notes

Reaction equation

HRID 352557 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:7]=[O:8])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.Cl>C1COCC1>[CH:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 98989903-Isopropyl-4-methoxybenzaldehydeHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10976088[4-Methoxy-3-(propan-2-yl)phenyl]methanolYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-isopropyl-4-methoxy-benzaldehyde (1.5 g, 8.42 mmol) in anhydrous THF (17 mL) cooled to -78° C. with a dry ice-acetone bath was added diisobutylaluminum hydride (34 mL, 1.0 M solution in THF, 34 mmol). After 1.5 h of cooling, 1N HCl (30 mL) was slowly added to the mixture. After the addition, the cooling bath was removed and the mixture left to stir at RT (ca. 15 min). The product was extracted with EtOAc (100 mL). The EtOAc extract was washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated in vacuo to give 1.405 g of colorless oil as crude product. The crude product was purified by chromatography using the ISCO Combiflash SQ16X system (35 g Redisep silica gel column, 0 to 40% EtOAc in hexane for 30 min at 30 mL/min) to afford 1.272 g (84%) of compound 55 as a colorless oil.

Workup

  1. temperatureAfter 1.5 h of cooling
  2. additionAfter the addition
  3. customthe cooling bath was removed
  4. waitthe mixture left
  5. extractionThe product was extracted with EtOAc (100 mL)
  6. extractionThe EtOAc extract
  7. washwas washed with brine (50 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23932688d67c4228a6c80093a313cd63
Source dataset
uspto-grants-2004_06
Patent number
US06747048B2

Reaction notes

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