Methyl 4-(benzyloxy)-3-chlorobenzoate → (4-Benzyloxy-3-chloro-phenyl)-methanol

HRID 19917Notes

Reaction equation

HRID 19917 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([Cl:18])[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][C:6]=1[Cl:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 21044521Methyl 4-(benzyloxy)-3-chlorobenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 21976852(4-Benzyloxy-3-chloro-phenyl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-benzyloxy-3-chloro-benzoic acid methyl ester (CAB02121, 4.15 g, 15.0 mmol) in THF (30 mL) was added slowly with a syringe to a suspension of lithium aluminium hydride (1.0 g, 26.3 mmol) in THF (30 mL). The reaction mixture was stirred for 30 minutes at room temperature and then carefully quenched by addition of 2N sodium hydroxide solution in water. After 20 minutes stirring the colour of the mixture turned from grey to white. The white precipitate was filtered off, the filtrate was dried over sodium sulphate and concentrated under reduced pressure to give an colourless oil, which was used without further purification. Yield: 3.61 g (97%). 1H-NMR (400 MHz, CDCl3) δ=2.12 (s, 1H, —OH), 4.56 (s, 2H), 5.16 (s, 2H), 6.93 (d, J=8.6 Hz, 1H), 7.14 (dd, J=8.6, 2.3 Hz, 1H), 7.31-7.48 (m, 6H).

Workup

  1. customcarefully quenched by addition of 2N sodium hydroxide solution in water
  2. stirringAfter 20 minutes stirring the colour of the mixture
  3. filtrationThe white precipitate was filtered off
  4. dry with materialthe filtrate was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto give an colourless oil, which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-e85abea422bf4f27be534150cd0d5c9a
Source dataset
uspto-grants-2010_06
Patent number
US07745472B2

Reaction notes

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