Hydrochloric Acid → HCID 67019298, compound

HRID 1753993Notes

Reaction equation

HRID 1753993 reaction equation
C[O:2][C:3]1[CH:8]([CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]([O:14]C)=[CH:6][CH2:5][CH:4]=1.Cl>O>[CH3:12][CH:11]([CH3:13])[CH2:10][CH2:9][CH:8]1[C:7](=[O:14])[CH2:6][CH2:5][CH2:4][C:3]1=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67019293HCID 67019293, compound

Product 1

HCID 67019298HCID 67019298, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of ether 6 (84.0 g, 400 mmol) and 1N HCl (25 mL) was heated to 90° C. while stirring vigorously. After about 15 minutes the mixture became exothermic and a clear homogeneous liquid resulted. The reaction mixture was stirred for an additional 15 minutes at this temperature and cooled to room temp. During this process the product solidified, and the mixture was diluted with water (500 mL) and filtered. The solid was suspended in hexanes (250 mL), stirred, filtered and dried to give 68.0 g (93.4%) of 7. MS m/z 183 (M+1); 1H NMR (300 MHz, CDCl3) δ 9.5-9.0 (br s, 1H), 2.5 (t, 4H), 2.3-2.2 (m, 2H), 2.0-1.9 (m, 2H), 1.6-1.5 (m, 1H), 1.2-1.1 (m, 2H), 0.9 (d, 6H); 13C NMR (CDCl3) δ 206.0, 188.1, 117.2, 40.1, 38.1, 33.3, 28.6, 23.0, 21.2, 20.2

Workup

  1. customa clear homogeneous liquid resulted
  2. stirringThe reaction mixture was stirred for an additional 15 minutes at this temperature
  3. temperaturecooled to room temp
  4. filtrationfiltered
  5. stirringstirred
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-43a5a7cc069a4510af5edf778673b9af
Source dataset
uspto-grants-2015_10
Patent number
US09169190B2

Reaction notes

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