Aluminium lithium hydride → HCID 67069097, compound

HRID 1422864Notes

Reaction equation

HRID 1422864 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-f8c91f669f98414db536e30b29cec506
Source dataset
uspto-grants-2015_01
Patent number
US08927548B2

Reaction notes

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