Sodium Hydroxide → HCID 896963, compound

HRID 19928Notes

Reaction equation

HRID 19928 reaction equation
C([O:8][C:9](=O)[C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([Cl:26])[CH:11]=1)C1C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[CH2:19]([O:18][C:13]1[C:14]([O:16][CH3:17])=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][C:12]=1[Cl:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 16749113HCID 16749113, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 896963HCID 896963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-benzyloxy-3-chloro-5-methoxy-benzoic acid benzyl ester (CAB02162, 3.83 g, 10.0, mmol) in THF (20 mL) was added dropwise with a syringe to a suspension of lithium aluminium hydride (500 mg, 13.15 mmol) in THF (30 mL). The mixture was stirred at room temperature for 30 minutes and 2N NaOH (5 mL) was added. The mixture was stirred for another hour, the aluminium salts were filtered off, the filtrate was dried over sodium sulphate and concentrated under reduced pressure. The resulting oil was heated to 120° C. under high vacuum in a kugelrohr-destillation-apparatus to remove benzyl alcohol for 10 h. The product was obtained as a light yellow oil and was used without any further purification. Yield: 2.70 g (97%). 1H-NMR (400 MHz, CDCl3) δ=2.09 (2, 1H, —OH), 3.86 (s, 3H, —OCH3), 4.56 (s, 2H), 5.02 (s, 2H), 6.83 (d, J=2.0 Hz, 1H), 6.95 (d, J=2.0 Hz, 1H), 7.31-7.41 (m, 3H), 7.52-7.55 (m, 2H).

Workup

  1. stirringThe mixture was stirred for another hour
  2. filtrationthe aluminium salts were filtered off
  3. dry with materialthe filtrate was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. temperatureThe resulting oil was heated to 120° C. under high vacuum in a kugelrohr-destillation-apparatus
  6. customto remove benzyl alcohol for 10 h
  7. customThe product was obtained as a light yellow oil
  8. customwas used without any further purification

Sources & evidence

ORD record
ord-3fbb317baea144ad936b84bf7315b8cf
Source dataset
uspto-grants-2010_06
Patent number
US07745472B2

Reaction notes

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