Water → HCID 10867554, compound

HRID 638139Notes

Reaction equation

HRID 638139 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([OH:14])[CH3:13].[OH2:15]>S(=O)(=O)(O)O>[O:14]=[C:12]([CH3:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]#[C:4][CH2:3][C:2]([OH:15])=[O:1]

Participants

4

Reactant 2

HCID 962WaterHCID 20253400HCID 20253400, compound

Product 1

HCID 10867554HCID 10867554, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
23 °C

Procedure

To a vigorously stirred, ice-cold solution of chromic trioxide (5.4 g, 54 mmol) in 50 mL of 6N sulfuric acid was added dropwise over 3 hr, 1.76 g (8.9 mmol) of 20 in 50 mL of acetone5. The reaction was kept in an ice-bath for 30 min and then warmed to 23° C. before workup. Water (200 mL) was added and the reaction extracted with ether (4×75 mL). The ether extract was washed with brine (3×50 mL). Product isolation yielded crude 11-keto-3-dodecynoic acid (23) which was purified by crystallization from 10% ether in hexane (mp 49°-51° C.) to yield 1.28 g (68% yield).

Workup

  1. extractionthe reaction extracted with ether (4×75 mL)
  2. extractionThe ether extract
  3. washwas washed with brine (3×50 mL)

Sources & evidence

ORD record
ord-9188183f4a8c4336affba179360eee5d
Source dataset
uspto-grants-1985_12
Patent number
US04560551

Reaction notes

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