Dichloromethane → (3,4,5-Tris(benzyloxy)phenyl)methanol

HRID 1760893Notes

Reaction equation

HRID 1760893 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:5]=1.[Li].C(Cl)Cl>C1COCC1>[CH2:27]([O:26][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:3][OH:2])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 352181Methyl 3,4,5-Tris(benzyloxy)benzoateHCID 3028194Lithium2×

Product 1

HCID 11407668(3,4,5-Tris(benzyloxy)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 20.0 g (0.044 mol) of 3,4,5-trisbenzyloxybenzoic acid methyl ester in 100 ml of THF is added dropwise with vigorous stirring, over a period of 60 minutes at room temperature, to a suspension of 4.00 g (0.11 mol) of lithium alanate in 100 ml of THF, in the course of which the temperature rises to 65° C. (reflux). After a further 2 hours at reflux, excess lithium alanate is cautiously hydrolysed, and the product is isolated in customary manner by extraction with methylene chloride. Amorphous powder, yield 12.0 g (64% of theory).

Workup

  1. customrises to 65° C.
  2. temperature(reflux)
  3. temperatureAfter a further 2 hours at reflux

Sources & evidence

ORD record
ord-32f0a52912d94b1695dfeab39376e228
Source dataset
uspto-grants-2005_01
Patent number
US06846492B2

Reaction notes

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