Ethanol → (4-(2,2-Diethoxyethoxy)-2,5-dimethylphenyl)methanol

HRID 471004Notes

Reaction equation

HRID 471004 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][CH:10]([O:25][CH2:26][CH3:27])[CH2:11][O:12][C:13]1[C:22]([CH3:23])=[CH:21][C:16]([C:17](OC)=[O:18])=[C:15]([CH3:24])[CH:14]=1)[CH3:8].C(O)C>C1COCC1>[CH2:26]([O:25][CH:10]([O:9][CH2:7][CH3:8])[CH2:11][O:12][C:13]1[C:22]([CH3:23])=[CH:21][C:16]([CH2:17][OH:18])=[C:15]([CH3:24])[CH:14]=1)[CH3:27]

Participants

5

Reactant 3

HCID 702EthanolHCID 21226445Aluminium lithium hydrideHCID 57988923HCID 57988923, compound

Product 1

HCID 57989312(4-(2,2-Diethoxyethoxy)-2,5-dimethylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride solution (1M in THF, 1.17 mL) was added dropwise to a solution of methyl 4-(2,2-diethoxyethoxy)-2,5-dimethylbenzoate (example 18, step c) (0.231 g) in THF (20 mL) at 0° C. The resulting mixture was allowed to warm to RT and stirred for 1 h. Ethanol (0.5 mL) was cautiously added and the reaction concentrated. The residue was partitioned between 1M NaOH (50 mL) and ethyl acetate (100 mL). The aqueous was separated and extracted with ethyl acetate (2×50 mL). The combined organics were washed with brine (50 mL), dried over magnesium sulphate, filtered and evaporated to give the subtitled compound as a clear oil. Yield 0.20 g.

Workup

  1. concentrationthe reaction concentrated
  2. customThe residue was partitioned between 1M NaOH (50 mL) and ethyl acetate (100 mL)
  3. customThe aqueous was separated
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe combined organics were washed with brine (50 mL)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-1d1df813470348a8a1a9002fb59094d8
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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