Water → HCID 66671213, compound

HRID 1877713Notes

Reaction equation

HRID 1877713 reaction equation
[Br-].[CH2:2]([O:9][CH2:10][CH2:11][CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[Br:38][C:39]1[CH:40]=[CH:41][C:42]([OH:47])=[C:43]([CH:46]=1)[CH:44]=O.O>C1COCC1>[CH2:2]([O:9][CH2:10][CH2:11][CH:12]=[CH:44][C:43]1[CH:46]=[C:39]([Br:38])[CH:40]=[CH:41][C:42]=1[OH:47])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 728635-BromosalicylaldehydeHCID 10929077(3-Benzyloxypropyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 66671213HCID 66671213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

60.0 g (122 mmol) of (3-benzyloxypropyl)triphenylphosphonium bromide are initially introduced in 400 ml of THF, and a solution of 25.0 g (223 mmol) of potassium tert-butoxide in 100 ml of THF is added dropwise at −10° C. A solution of 20.0 g (99.5 mmol) of 5-bromo-2-hydroxybenzaldehyde in 200 ml of THF is subsequently added dropwise at 0° C., and the batch is stirred overnight at room temp. The reaction mixture is subsequently hydrolysed using water and extracted three times with MTB ether. The combined org. phases are washed with water and sat. sodium chloride soln. and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is filtered through silica gel with heptane/ethyl acetate (4:1), giving a mixture of cis- and trans-2-(4-benzyloxybut-1-enyl)-4-bromophenol as a colourless oil, which is reacted without further purification.

Workup

  1. extractionextracted three times with MTB ether
  2. washphases are washed with water and sat. sodium chloride soln
  3. dry with materialand dried over sodium sulfate
  4. customThe solvent is removed in vacuo
  5. filtrationthe residue is filtered through silica gel with heptane/ethyl acetate (4:1)
  6. customgiving
  7. customis reacted without further purification

Sources & evidence

ORD record
ord-efe2f03d1bf54a129b0a0dd1a005d7a3
Source dataset
uspto-grants-2012_11
Patent number
US08313669B2

Reaction notes

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