Hydrochloric Acid → (3-Chloro-5-methoxyphenyl)methanol

HRID 1983216Notes

Reaction equation

HRID 1983216 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:5](O)=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 129093413-Chloro-5-methoxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 12909342(3-Chloro-5-methoxyphenyl)methanolYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 38a (1.0 g, 5.36 mmol, 1.0 equiv.) in 30 mL of THF was added LAH (0.20 g, 5.36 mmol, 1.0 equiv.) in several portions. The mixture was stirred at room temperature for 2 h, and poured into 50 mL of 1M aqueous HCl. The aqueous layer was extracted twice with 30 mL of EtOAc. The combined EtOAc extracts were washed with 40 mL of saturated NaHCO3, 40 mL of brine, dried over Na2SO4, and evaporated in vacuo to give 0.8 g of a white solid. 1H-NMR (DMSO-d6): δ 6.93 (s, 1H), 6.87 (m, 1H), 6.85 (m, 1H), 5.32 (t, J=5.8 Hz, 1H), 4.46 (d, J=6.0 Hz, 2H), 3.76 (s, 3H).

Workup

  1. extractionThe aqueous layer was extracted twice with 30 mL of EtOAc
  2. washThe combined EtOAc extracts were washed with 40 mL of saturated NaHCO3, 40 mL of brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-2210e8cda9bc4ba59377a3b695f99322
Source dataset
uspto-grants-2009_06
Patent number
US07541383B2

Reaction notes

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