2,2-Dimethoxypropane → Methyl 1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 1656044

Reaction equation

HRID 1656044 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=[O:12].[CH3:14]OC(OC)(C)C>CO>[C:11]([CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 1013701,2,3,4-Tetrahydro-2-naphthoic acid

Product 1

HCID 12588372Methyl 1,2,3,4-tetrahydronaphthalene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Dissolve 1,2,3,4-tetrahydro-2-naphthoic acid (10 g, 57 mmol) in methanol (100 mL) and add dimethoxypropane (3 mL). Cool to 5° C. and saturate with hydrogen chloride gas. Allow to stand overnight then evaporate the solvent in vacuo. Take the residue up in ethyl ether, wash with saturated sodium hydrogen carbonate and dry (MgSO4). Evaporate the solvent in vacuo and distill to give 2-carbomethoxy-1,2,3,4-tetrahydronaphthalene; bp 90°-96° [email protected] mm Hg).

Workup

  1. concentrationsaturate with hydrogen chloride gas
  2. customthen evaporate the solvent in vacuo
  3. washwash with saturated sodium hydrogen carbonate
  4. dry with materialdry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. distillationdistill

Sources & evidence

ORD record
ord-468bb5f1f93a4377951a1538f2606c3e
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Linked notes

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