Hydrochloric Acid → Methyl 3-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate

HRID 126959Notes

Reaction equation

HRID 126959 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.Cl.[CH3:16]O>>[CH3:16][O:13][C:12]([C:3]1[C:2]([OH:1])=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=1)=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2259274225435-10-3

Product 1

HCID 265142Methyl 3-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Procedure

A 281 g sample of 3-hydroxy-5,6,7,8-tetrahydro-2-naphthoic acid was dissolved in 1.4 l of methanol, and while hydrogen chloride gas was supplied, the solution was first exposed to room temperature for 2 hours, and then heated at 60° to 70° C. for 4 hours. Methanol was distilled off under vacuum, water was added to the residue, which was then extracted with ethyl acetate. The ethyl acetate layer was washed with sodium bicarbonate until it became neutral, and then it was dehydrated and concentrated. The residual oily product was distilled under vacuum to provide 279 g of the title compound (1) having the following physical properties.

Workup

  1. temperatureheated at 60° to 70° C. for 4 hours
  2. distillationMethanol was distilled off under vacuum, water
  3. additionwas added to the residue, which
  4. extractionwas then extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with sodium bicarbonate until it
  6. concentrationconcentrated
  7. distillationThe residual oily product was distilled under vacuum

Sources & evidence

ORD record
ord-757bb95cabbf499388fade1466d643d1
Source dataset
uspto-grants-1981_03
Patent number
US04254056

Reaction notes

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