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Hydrochloric Acid → 4-[2-(4,4-Dimethyl-chroman-7-yl)-heptyloxy]-benzoic acid

HRID 2415186
Notes
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Reaction equation

HRID 2415186 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]([C:18]2[CH:27]=[C:26]3[C:21]([C:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25]3)=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1.[OH-].[K+].C1COCC1.Cl>C(O)C.O>[CH3:28][C:22]1([CH3:29])[C:21]2[C:26](=[CH:27][C:18]([CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][O:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:30])=[O:2])=[CH:9][CH:8]=3)=[CH:19][CH:20]=2)[O:25][CH2:24][CH2:23]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 121490674-[2-(4,4-Dimethyl-chroman-7-yl)-heptyloxy]-benzoic acid methyl ester

Product 1

HCID 101788924-[2-(4,4-Dimethyl-chroman-7-yl)-heptyloxy]-benzoic acidYield 79.4%

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 4-[2-(4,4-dimethyl-chroman-7-yl)-heptyloxy]-benzoic acid methyl ester (0.474 g, 1.15 mmole) in 8 mL of ethanol was treated with a solution of potassium hydroxide (1.3 g) in 5 mL of water. THF (4 mL) was added and the mixture was heated at 45° C. for two hours, diluted with 20 mL of water and the pH was adjusted to 2 with concentrated HCl. The mixture was then extracted with three 20 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow foam. The product was purified by recrystallization from acetonitrile/water to yield 0.362 g of 4-[2-(4,4-dimethyl-chroman-7-yl)-heptyloxy]-benzoic acid (1) as a white solid. M.p.: 91.5-93.3° C.

Workup

  1. extractionThe mixture was then extracted with three 20 mL portions of ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a pale yellow foam
  6. customThe product was purified by recrystallization from acetonitrile/water

Sources & evidence

ORD record
ord-d3f9ebadae2a474789021ad2ce4d1fb1
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06818652B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes