HCID 10904699, compound → HCID 11131640, compound

HRID 991976Notes

Reaction equation

HRID 991976 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:24])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=1)[C:5](OC)=[O:6].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:24])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:22])[CH3:23])[CH:14]=1)[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 10904699HCID 10904699, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 11131640HCID 11131640, compoundYield 115.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3,5-dichloro-4-(4-methoxy-3-isopropyl-phenoxy)benzoate (Example 5a) (3.0 g) was treated with a 1 M solution of diisobutyl aluminium hydride (DIBAL) in THF (32.5 ml) at 0° C. and then warmed to room temperature and stirred overnight. The reaction mixture was poured into an ice-cold 1 M HCl solution and extracted with ethyl acetate three times. The organic layer was washed (brine), dried, filtered and concentrated to dryness affording 3,5-dichloro-4-(4-methoxy-3-isopropylphenoxy)benzylalcohol (3.21 g, 100%) as an oil.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer was washed (brine)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-765f82e48e594683ae8ba8f0a2e5a621
Source dataset
uspto-grants-2002_10
Patent number
US06465687B1

Reaction notes

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