Aluminium lithium hydride → HCID 67069097, compound

HRID 1881370Notes

Reaction equation

HRID 1881370 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([Br:26])=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([Br:26])=[CH:14][C:10]=1[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 469156382,4-Bis(benzyloxy)-5-bromobenzoic acid

Product 1

HCID 67069097HCID 67069097, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with 2,4-bis-benzyloxy-5-bromobenzoic acid (12.4 g; 30 mmol) and tetrahydrofuran (200 mL) and stirred under nitrogen until the solution was homogeneous. Lithium aluminum hydride (1.425 g; 1.25 eq.) was slowly added and the reaction was stirred until TLC indicated that the starting material had been consumed. The reaction was slowly quenched with a saturated solution of sodium sulfate (20 mL) and then filtered through celite. The solid was washed with an additional charge of tetrahydrofuran (100 mL), and the organic layers were evaporated to give 2,4-bis-benzyloxy-5-bromobenzyl alcohol (10.5 g; 26 mmol).

Workup

  1. stirringthe reaction was stirred until TLC
  2. customhad been consumed
  3. customThe reaction was slowly quenched with a saturated solution of sodium sulfate (20 mL)
  4. filtrationfiltered through celite
  5. washThe solid was washed with
  6. additionan additional charge of tetrahydrofuran (100 mL)
  7. customthe organic layers were evaporated

Sources & evidence

ORD record
ord-6eb7283633e346099387490903e4fcd2
Source dataset
uspto-grants-2012_11
Patent number
US08318790B2

Reaction notes

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