Benzene → HCID 20365468, compound

HRID 1678971Notes

Reaction equation

HRID 1678971 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1)([CH3:10])[C:7]([OH:9])=[O:8].[CH:24]1C=CC=C[CH:25]=1>C(N(CC)CC)C>[CH3:10][C:6]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)=[CH:14][CH:13]=1)([CH3:5])[C:7]([O:9][CH2:24][CH3:25])=[O:8]

Participants

5

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 203654692-Methyl-2-[4-(oxan-4-yl)phenoxy]propanoic acid

Product 1

HCID 20365468HCID 20365468, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.2 ml of thionyl chloride were added at 15° C to a mixture of 7 g of 2-methyl-2-[p-(4-tetrahydropyranyl)-phenoxy]-propanoic acid, 70 ml of benzene and 3.5 ml of triethylamine and the mixture was stirred for 2 hours at room temperature and was then filtered. The filtrate was slowly added to 250 ml of 5.4N hydrochloric acid in ethanol and the mixture was stirred for 12 hours at room temperature and was then concentrated to dryness. The residue was added to 100 ml of ether and the solution was washed with a saturated sodium bicarbonate solution and then with water. The solution was dried and evaporated to dryness and the oily residue was distilled under reduced pressure to obtain 6.5 g of ethyl 2-methyl-2-[p-(4-tetrahydropyranyl)-phenoxy]-propanoate with a boiling point of 138°-140° C at 0.1 mm Hg.

Workup

  1. filtrationwas then filtered
  2. additionThe filtrate was slowly added to 250 ml of 5.4N hydrochloric acid in ethanol
  3. stirringthe mixture was stirred for 12 hours at room temperature
  4. concentrationwas then concentrated to dryness
  5. additionThe residue was added to 100 ml of ether
  6. washthe solution was washed with a saturated sodium bicarbonate solution
  7. customThe solution was dried
  8. customevaporated to dryness
  9. distillationthe oily residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-1a7018938cb34854bfa5691f927a5793
Source dataset
uspto-grants-1978_03
Patent number
US04078076

Reaction notes

Loading…