Lithium Hydroxide → HCID 9903533, compound

HRID 1583026Notes

Reaction equation

HRID 1583026 reaction equation
[OH-].[Li+].[C:3]1([CH2:9][CH2:10][O:11][C:12]2[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][C:13]=2[C:14]([O:16]CCC2C=CC=CC=2)=[O:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OCC)(=O)C>O.O1CCCC1.CO>[C:3]1([CH2:9][CH2:10][O:11][C:12]2[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][C:13]=2[C:14]([OH:16])=[O:15])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 22716779HCID 22716779, compound

Product 1

HCID 9903533HCID 9903533, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (4.32 g, 0.18 mol, 3 eq) in water (80 mL) was added to a stirred solution of 2-phenylethyl 2-(2-phenylethoxy)-5-formylbenzoate (22.46 g, 0.06 mol, 1 eq) in a mixture of tetrahydrofuran (240 mL) and methanol (80 mL). The reaction mixture was stirred for 3 h, then concentrated in vacuo, and the residue diluted with water (100 mL), and washed with ethyl acetate (2×100 mL). The aqueous solution was acidified to pH 1 with concentrated HCl, extracted with ethyl acetate (2×100 mL), and the organic solution dried over sodium sulfate and evaporated. This gave a gummy solid, which was recrystallized from ethyl acetate and ether to give a pale yellow powder (8.87 g, 55% (2 steps)). RF (petroleum ether:ethyl acetate, 2:1) 0.35. 1H NMR (CDCl3) δ9.97 (s, 1H, O═C—H), 8.65 (d, 1H, J 2.3 Hz, ArH), 8.11 (dd, 1H, J 8.7 and 2.3 Hz, ArH), 7.18 (d, 1H, J 8.7 Hz, ArH), 4.58 (t, 2H, J 6.8 Hz, OCH2CH2Ph), 3.27 (t, 2H, J 6.8 Hz, OCH2CH2Ph).

Workup

  1. concentrationconcentrated in vacuo
  2. additionthe residue diluted with water (100 mL)
  3. washwashed with ethyl acetate (2×100 mL)
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. dry with materialthe organic solution dried over sodium sulfate
  6. customevaporated
  7. customThis gave a gummy solid, which
  8. customwas recrystallized from ethyl acetate and ether
  9. customto give a pale yellow powder (8.87 g, 55% (2 steps))

Sources & evidence

ORD record
ord-03145ed831a048ef99c2a39b3331f624
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

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