Hydrochloric Acid → 3,4-Dihydro-2-hydroxy-3-(2-propenyl)-naphthalenecarboxylic Acid, Methyl Ester

HRID 1421893Notes

Reaction equation

HRID 1421893 reaction equation
[OH:1][C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[CH:16]([N-]C(C)C)([CH3:18])[CH3:17].[Li+].C(Br)C=C.Cl>O1CCCC1>[OH:1][C:2]1[CH:11]([CH2:18][CH:16]=[CH2:17])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 2724682Lithium diisopropylamideHCID 546921643,4-Dihydro-2-hydroxynaphthalenecarboxylic Acid, Methyl Ester

Product 1

HCID 546808303,4-Dihydro-2-hydroxy-3-(2-propenyl)-naphthalenecarboxylic Acid, Methyl EsterYield 106.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3,4-dihydro-2-hydroxynaphthalene carboxylic acid, methyl ester (36.2 g, 177 mmol) in dry tetrahydrofuran (440 ml) at -30° C. under argon was added dropwise lithium diisopropylamide (195 ml, 2M solution, 390 mmol). Allyl bromide (24.3 ml, 284 mmol) was then added at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 1 h, then treated with hydrochloric acid (5M) to pH2-3. The resulting mixture was extracted with ethyl acetate (2×1000 ml) and the combined extracts were washed with brine (1000 ml), dried (Na2SO4) and evaporated in vacuo to give the title compound as a brown oil (46.1 g).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (2×1000 ml)
  2. washthe combined extracts were washed with brine (1000 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a0c087aa6d9d4450b206d577f088f4f1
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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