2,6-Di(propan-2-yl)benzoyl chloride → [2,6-Di(propan-2-yl)phenyl]methanol

HRID 2393267Notes

Reaction equation

HRID 2393267 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]([CH3:15])[CH3:14])[C:5]=1[C:6](Cl)=[O:7])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[CH2:6][OH:7])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 130685852,6-Di(propan-2-yl)benzoyl chlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 45117178[2,6-Di(propan-2-yl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,6-diisopropylbenzoyl chloride (11.65 g, 0.052 mol), in ethyl ether (100 mL) was added over 20 minutes to a suspension of lithium aluminum hydride (1.9 g, 0.050 mol) in ethyl ether (200 mL) keeping the temperature below -15° C. The reaction mixture was allowed to slowly warm to room temperature and was then cooled to zero. The reaction was quenched by careful addition of sodium bisulfate solution until no further reaction was evident. The mixture was diluted with ether (200 mL), the ether washed with brine. The grey goo (lithium/aluminum salts) was washed several times with ether, the ether washes were combined, dried (magnesium sulfate), filtered, and concentrated to an oil which solidified, 10.67 g.

Workup

  1. customthe temperature below -15° C
  2. temperaturewas then cooled to zero
  3. customThe reaction was quenched by careful addition of sodium bisulfate solution until no further reaction
  4. additionThe mixture was diluted with ether (200 mL)
  5. washthe ether washed with brine
  6. washThe grey goo (lithium/aluminum salts) was washed several times with ether
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated to an oil which

Sources & evidence

ORD record
ord-f5f642bdb100445fa822779ecb60121e
Source dataset
uspto-grants-1998_09
Patent number
US05807846

Reaction notes

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