Hydrochloric Acid → (E)-3-(4-bromophenyl)but-2-en-1-ol

HRID 984313Notes

Reaction equation

HRID 984313 reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21](/[C:24](/[CH3:31])=[CH:25]/[C:26](OCC)=[O:27])=[CH:20][CH:19]=1.Cl>C1COCC1.CO>[Br:17][C:18]1[CH:19]=[CH:20][C:21](/[C:24](/[CH3:31])=[CH:25]/[CH2:26][OH:27])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 15933615(E)-ethyl 3-(4-bromophenyl)-but-2-enoate

Product 1

HCID 69361278(E)-3-(4-bromophenyl)but-2-en-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of DIBAL-H in toluene (42 ml, 42 mmol) was added dropwise, at −70° C. over 30 min, to a stirred solution of (E)-ethyl 3-(4-bromophenyl)-but-2-enoate (4.55 g, 16.92 mmol) in dry THF (100 ml), and the mixture stirred for 1 h. Methanol (5 ml) was carefully added, followed by 1N HCl (300 ml) and the resulting mixture extracted with ethyl acetate (3×200 ml). The combined organic extracts were washed with brine, dried (Na2SO4), and evaporated to give the crude product as an off-white solid, which was purified by recrystallisation from hot 1:4 ether/n-heptane (250 ml) to give the product (E)-3-(4-bromophenyl)-but-2-en-1-ol as colourless needles: 3.10 g (81%)

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate (3×200 ml)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give the crude product as an off-white solid, which
  6. customwas purified by recrystallisation from hot 1:4 ether/n-heptane (250 ml)

Sources & evidence

ORD record
ord-bddddbe0a08346da9d1bd6e04dbb74ee
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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