Dichloromethane → HCID 15389066, compound

HRID 1003635Notes

Reaction equation

HRID 1003635 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-2,5cyclohexadien-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-2,5cyclohexadien-1-ylidene)-1-propynyl]benzoic acid are collected, with a melting point of 216-8° C.

Sources & evidence

ORD record
ord-2229754ff1354c94833b411af63c4496
Source dataset
uspto-grants-2000_04
Patent number
US06046220

Reaction notes

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