Methyl 4-(benzyloxy)-3,5-dichlorobenzoate → (4-Benzyloxy-3,5-dichlorophenyl)methanol

HRID 19912Notes

Reaction equation

HRID 19912 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([Cl:19])[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:12]([O:11][C:7]1[C:6]([Cl:19])=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][C:8]=1[Cl:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 16749549Methyl 4-(benzyloxy)-3,5-dichlorobenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 16749116(4-Benzyloxy-3,5-dichlorophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-benzyloxy-3,5-dichloro-benzoic acid methyl ester (CAB02115, 7.20 g, 23.14 mmol) in THF (20 mL) was added slowly with a syringe to a suspension of lithium aluminium hydride (1.50 g, 39.5 mmol) in THF (40 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. The residue was recrystallised from dichloromethane/hexane. Yield: 5.83 g (89%) white powder. 1H-NMR (400 MHz, CDCl3) δ 1.85 (t, J=5.9 Hz, 1H, —OH), 4.63 (d, J=5.9 Hz, 2H), 5.04 (s; 2H), 7.33 (s, 2H), 7.35-7.44 (m, 3H), 7.55-7.59 (m, 2H). 13C-NMR (100 MHz, CDCl3) δ=64.05, 75.03, 127.36, 128.70, 128.75, 129.91, 136.39, 138.64, 150.32.

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. customThe residue was recrystallised from dichloromethane/hexane

Sources & evidence

ORD record
ord-0e0dae581352442ca1a8125ef1d7ad70
Source dataset
uspto-grants-2010_06
Patent number
US07745472B2

Reaction notes

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