Dichloromethane → HCID 15389066, compound

HRID 428209Notes

Reaction equation

HRID 428209 reaction equation
O[CH:2]([C:14]1[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:17]([O:24]COCC[Si](C)(C)C)=[C:16]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:15]=1)[C:3]#[C:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.ClCCl.FC(F)(F)C(O)=O>O>[C:33]([C:16]1[C:17](=[O:24])[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:19][C:14](=[CH:2][C:3]#[C:4][C:5]2[CH:6]=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:12][CH:13]=2)[CH:15]=1)([CH3:34])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 15389065HCID 15389065, compound

Product 1

HCID 15389066HCID 15389066, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.2 g (4.7 mmol) of 4-{3-Hydroxy-3-[3,5-di-tert-butyl-4-(2-trimethylsilylethoxymethoxy)phenyl]-1-propynyl}benzoic acid and 75 ml of dichloromethane are introduced into a three-necked flask. 360 μl (4.7 mmol) of trifluoroacetic acid are added at −78° C. and the mixture is allowed to return to room temperature. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is triturated from heptane, filtered and then dried. 1.6 g (90%) of 4-[3-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-1-propynyl]benzoic acid are collected, with a melting point of 216-8° C.

Workup

  1. customto return to room temperature
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis triturated from heptane
  8. filtrationfiltered
  9. customdried
  10. custom1.6 g (90%) of 4-[3-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-1-propynyl]benzoic acid are collected, with a melting point of 216-8° C.

Sources & evidence

ORD record
ord-f3e19097c01a409db56a4c8f552ff165
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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