Benzyl 2-benzyloxy-3-isopropylbenzoate → 2-Benzyloxy-3-isopropylbenzylalcohol

HRID 1739474Notes

Reaction equation

HRID 1739474 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[C:30]([CH:31]([CH3:33])[CH3:32])=[CH:29][CH:28]=[CH:27][C:16]=1[C:17](OCC1C=CC=CC=1)=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([O:14][C:15]1[C:30]([CH:31]([CH3:33])[CH3:32])=[CH:29][CH:28]=[CH:27][C:16]=1[CH2:17][OH:18])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 13791537Benzyl 2-benzyloxy-3-isopropylbenzoateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 218409612-Benzyloxy-3-isopropylbenzylalcoholYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of LiAlH4 (1M in THF, 8.13 ml) was added to freshly distilled THF (10 ml) 10 ml. A solution of benzyl 2-benzyloxy-3-isopropylbenzoate (2.27 g, 6.31 mmole) in THF (10 ml) was added via a syringe to the LiAlH4 solution. The temperature was maintain below 40° C. using a water bath and the reaction mixture stirred at ambient temperature overnight. The reaction was quenched with water and the pH adjusted to ~7 with dilute HCl. The resultant precipitate was filtered off and the filtrate partitioned between ethyl acetate/H2O. The organic phase was dried (MgSO4), evaporated and the residue purified by chromatography (eluant: ethyl acetate/hexane) to give 2-benzyloxy-3-isopropylbenzylalcohol (1.38 g, 83%).

Workup

  1. temperatureThe temperature was maintain below 40° C.
  2. customThe reaction was quenched with water
  3. filtrationThe resultant precipitate was filtered off
  4. customthe filtrate partitioned between ethyl acetate/H2O
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated
  7. customthe residue purified by chromatography (eluant: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c7f65defc9dd4474987cd11126e1d7e6
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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