Hydrochloric Acid → HCID 56978419, compound

HRID 648783Notes

Reaction equation

HRID 648783 reaction equation
CC(C)([O-])C.[K+].[O:7]=[C:8]([CH3:27])[CH2:9][CH2:10][CH:11]([C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])[CH2:12][C:13]([O:15]C)=[O:14].Cl>C(O)(C)(C)C.O>[O:7]=[C:8]1[CH2:9][CH2:10][CH:11]([CH2:12][C:13]([OH:15])=[O:14])[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[CH:27]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 53912327HCID 53912327, compound

Product 1

HCID 56978419HCID 56978419, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent2×

Procedure

A solution of potassium t-butoxide (0.507 g.) in t-butanol (5 ml.) was added gradually to a stirred solution of (A) (1.2 g.) in t-butanol (10 ml.) maintained under an argon atmosphere and with external cooling to 20°-25° C. The resultant mixture was stirred for 15 minutes and then evaporated to give a sticky solid. This solid was dissolved in water. The resultant solution was acidified (1M HCl) to pH2 and extracted with ether. The extracts were shaken with 10% w/v sodium carbonate solution (3×20 ml.). The combined carbonate extracts were acidified (1M HCl) to give (4-keto- 2-o-methoxyphenyl-cyclohex-2-enyl)acetic acid (B) as a solid precipitate (0.806 g.), m.p. 183°-184° C. NMR: 2.2 (7H,m), 3.5 (1H,m), 3.8 (3H,s), 6.05 (1H,d), 7.05 (4H,m) ppm.

Workup

  1. temperaturemaintained under an argon atmosphere
  2. temperaturewith external cooling to 20°-25° C
  3. customevaporated
  4. customto give a sticky solid
  5. extractionextracted with ether

Sources & evidence

ORD record
ord-896f3ef328994348963cf1df29236af7
Source dataset
uspto-grants-1988_04
Patent number
US04736057

Reaction notes

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