Hydrochloric Acid → 4,5,5-Trifluoro-2-(prop-2-en-1-yl)pent-4-en-1-ol

HRID 1987443Notes

Reaction equation

HRID 1987443 reaction equation
[C:1](=[C:4]([CH2:6][CH:7]([CH2:13][CH:14]=[CH2:15])[CH2:8][O:9]COC)[F:5])([F:3])[F:2].CO.Cl>O>[C:1](=[C:4]([CH2:6][CH:7]([CH2:13][CH:14]=[CH2:15])[CH2:8][OH:9])[F:5])([F:3])[F:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 714163061,1,2-Trifluoro-4-[(methoxymethoxy)methyl]hepta-1,6-diene

Product 1

HCID 714163054,5,5-Trifluoro-2-(prop-2-en-1-yl)pent-4-en-1-olYield 109.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

40 g of CF2═CFCH2CH(CH2OCH2OCH3)CH2CH═CH2 obtained in Example 3 and 100 mL of methanol were put into a 300 mL glass reactor, and a catalytic amount of concentrated hydrochloric acid was added thereto, followed by heating at 60° C. for 19 hours. The reaction solution was cooled to room temperature, and 30 mL of water was added to carry out liquid separation. The organic layer was further washed with 50 mL of water and subjected to precision distillation to obtain 35.3 g of CF2═CFCH2CH(CH2OH)CH2CH═CH2 (59-60° C./0.5 kPa).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customliquid separation
  3. washThe organic layer was further washed with 50 mL of water
  4. distillationsubjected to precision distillation

Sources & evidence

ORD record
ord-363678c7d2b34e12988f014078f041d8
Source dataset
uspto-grants-2009_06
Patent number
US07550545B2

Reaction notes

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