Hydrochloric Acid → HCID 21463694, compound

HRID 398308Notes

Reaction equation

HRID 398308 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:8][CH2:7][C:6]2[CH:9]=[C:10](/[CH:21]=[CH:22]/[C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29]CC)=[O:28])=[CH:25][CH:24]=3)[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][C:5]=2[CH2:4][CH2:3]1.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[CH3:34][C:2]1([CH3:1])[CH2:8][CH2:7][C:6]2[CH:9]=[C:10](/[CH:21]=[CH:22]/[C:23]3[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:32][CH:33]=3)[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][C:5]=2[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86759150HCID 86759150, compound

Product 1

HCID 21463694HCID 21463694, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The ester was dissolved in 20 ml of ethanol/tetrahydrofuran (1:1) and treated with 5.8 ml of 3N NaOH. Thereafter, the mixture was stirred at room temperature for 3 days, poured on to ice, acidified with 2N HCl, extracted with ethyl acetate, washed with water, dried and evaporated. Recrystallization from ethyl acetate yielded 1.56 g of (E)-4-[2-(7,7-dimethyl-3-octyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl)vinyl]benzoic acid as pale yellow crystals of melting point 179.5-180.5° C.

Workup

  1. additionpoured on to ice
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-c80b150d36b140189dcf437e42f148be
Source dataset
uspto-grants-2003_08
Patent number
US06610877B1

Reaction notes

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