Diisobutylaluminumhydride → (4-Chloro-3,5-diethoxyphenyl)methanol

HRID 1715140Notes

Reaction equation

HRID 1715140 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]([Cl:14])=[C:7]([O:15][CH2:16][CH3:17])[CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[Cl:14][C:8]1[C:9]([O:11][CH2:12][CH3:13])=[CH:10][C:5]([CH2:4][OH:3])=[CH:6][C:7]=1[O:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 596847734-Chloro-3,5-diethoxybenzoic acid ethyl ester

Product 1

HCID 67147397(4-Chloro-3,5-diethoxyphenyl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-3,5-diethoxy-benzoic acid ethyl ester (5.0 g, 18.33 mmol, 1.0 equiv) in dichloromethane (25 mL) was added slowly over a time period of 15 min under slight cooling to −30° C. a solution of diisobutylaluminum hydride (55.0 mL, 55.00 mmol, 3.0 equiv; 1.0 M solution in THF). After 30 min, the excess of hydride was quenched by cautious addition of methanol (10 mL) and water (2 mL). The mixture was stirred for 30 min, a solution of 1 M HCl was added and the aqueous layer extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over MgSO4 and concentrated by evaporation under reduced pressure providing 4.0 g (95%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.45 (t, J=7.0 Hz, 6H), 1.93 (br s, 1H), 4.09 (q, J=7.0 Hz, 4H), 4.62 (s, 2H), 6.57 (s, 2H). 13C NMR (75 MHz, CDCl3): δ 14.74, 64.96, 65.18, 104.30, 110.65, 140.29, 155.66. MS (ISP): 231.4 [M+H]−.

Workup

  1. customthe excess of hydride was quenched by cautious addition of methanol (10 mL) and water (2 mL)
  2. additiona solution of 1 M HCl was added
  3. extractionthe aqueous layer extracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-e63b3cdca4294a1cb95a5e4e47b9d32a
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

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