Water → 1,3-Di-tert-butyl-5-ethynylbenzene

HRID 1534094Notes

Reaction equation

HRID 1534094 reaction equation
[C:1]([O-])(C)(C)C.[K+].[Br-].BrC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:29]([C:33]1[CH:34]=[C:35]([CH:38]=[C:39]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:40]=1)[CH:36]=O)([CH3:32])([CH3:31])[CH3:30].O>O1CCCC1>[C:29]([C:33]1[CH:34]=[C:35]([C:36]#[CH:1])[CH:38]=[C:39]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:40]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 12682533,5-Bis(tert-butyl)benzaldehydeHCID 2733422Phosphonium, (bromomethyl)triphenyl-, bromide (1:1)HCID 23665647Potassium tert-butoxide

Product 1

HCID 114699511,3-Di-tert-butyl-5-ethynylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

73.7 g (0.655 mol) of potassium tert-butanolate were added a little at a time to 117.6 g (0.269 mol) of bromomethyltriphenylphosphonium bromide in 420 ml of dry tetrahydrofuran at 25° C. while cooling. The reaction mixture was then stirred for half an hour and, at -70° C., a solution of 50 g (0.218 mol) of 3,5-di-tertbutylbenzaldehyde in 120 ml of dry tetrahydrofuran was added dropwise. After half an hour, the mixture was allowed to warm to room temperature, and was then stirred overnight and poured into water. Extraction with ether, washing of the organic phase with water, drying over sodium sulfate and evaporation of the solvent produced a viscous residue.

Workup

  1. temperaturewhile cooling
  2. waitAfter half an hour
  3. temperatureto warm to room temperature
  4. stirringwas then stirred overnight
  5. extractionExtraction with ether
  6. washwashing of the organic phase with water
  7. dry with materialdrying over sodium sulfate and evaporation of the solvent
  8. customproduced a viscous residue

Sources & evidence

ORD record
ord-92a76e41835e46bc8bc1d3b39b0659bd
Source dataset
uspto-grants-1992_02
Patent number
US05087637

Reaction notes

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