3-(3-Bromophenyl)acrylic acid → 3-(3-Bromophenyl)propan-1-ol

HRID 454381

Reaction equation

HRID 454381 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[CH:11]=[CH:12][C:13](O)=[O:14]>C(OCC)C>[Br:7][C:8]1[CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][OH:14])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 362513-(3-Bromophenyl)acrylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 187859283-(3-Bromophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To suspension of LiAlH4 (0.5 g, 1.3 mmol) in diethyl ether (25 mL) was added 3-bromocinnamic acid (83, 1.0 g, 4 mmol), in portions, at RT. The resulting suspension was stirred for 3 hours. The reaction was quenched by the successive addition of 15% aq. NaOH solution (1 mL) and water. The resulting white suspension was filtered through a pad of Celite. The filter cake was washed with ether and then ethyl acetate. The filtrate was concentrated to afford crude 8 as yellow oil. Yield (0.7 g, 74%). 1H NMR (400 MHz, CDCl3) δ 7.10-7.35 (m, 4H), 3.65 (t, J=6.5 Hz, 2H), 2.68 (t, J=7.8 Hz, 2H), 1.82-1.91 (m, 2H).

Workup

  1. customat RT
  2. customThe reaction was quenched by the successive addition of 15% aq. NaOH solution (1 mL) and water
  3. filtrationThe resulting white suspension was filtered through a pad of Celite
  4. washThe filter cake was washed with ether
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8622a7861509441685223a31bd9c4f05
Source dataset
uspto-grants-2013_07
Patent number
US08492589B2

Linked notes

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