Formic Acid → HCID 53946128, compound

HRID 1389568Notes

Reaction equation

HRID 1389568 reaction equation
[Cl:1][CH2:2][C:3]([O:5][C@H:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]([CH:14]=[CH:15][C:16]([CH3:20])(O)[CH:17]=[CH2:18])=[C:8]([CH3:21])[C:7]1=[O:22])=[O:4].C(O)=[O:24].O>C(Cl)Cl>[Cl:1][CH2:2][C:3]([O:5][C@H:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]([CH:14]=[CH:15][C:16]([CH3:20])=[CH:17][CH2:18][OH:24])=[C:8]([CH3:21])[C:7]1=[O:22])=[O:4]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 54451447HCID 54451447, compound

Product 1

HCID 53946128HCID 53946128, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

47.8 g of 5-[4(S)-(chloroacetoxy)-3-oxo-2,6,6-trimethyl-cyclohex-1-en-1-yl]-3-methyl-penta-1,4-dien-3-ol are dissolved in 720 ml of methylene chloride. After the addition of 200 ml of formic acid, the solution is stirred at room temperture for 45 minutes, then introduced into water and extracted with diethyl ether. The ether extract is evaporated. The residue is taken up in 500 ml of methanol, treated with 100 g of potassium carbonate 250 ml of water, stirred for 1 hour, then introduced into water and extracted with ethyl acetate. The 5-[4(S)-(chloroacetoxy)-3-oxo-2,6,6-trimethyl-cyclohex-1-en-yl]-3-methyl-penta-2,4-dien-1-ol isolated from the extract is processed further as follows:

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe ether extract
  3. customis evaporated
  4. additiontreated with 100 g of potassium carbonate 250 ml of water
  5. stirringstirred for 1 hour
  6. additionintroduced into water
  7. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-80663b1fba6742b5b19bbbf9159caf45
Source dataset
uspto-grants-1981_01
Patent number
US04245109

Reaction notes

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